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PubMed Central is a free full-text archive of biomedical and life sciences journal literature at the U.S. National Institutes of Health's National Library of Medicine (NIH/NLM).

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by Made, Veronika; Els-Heindl, Sylvia; Beck-Sickinger, Annette G
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The great versatility and the inherent high affinities of peptides for their respective targets have led to tremendous progress for therapeutic applications in the last years. In order to increase the drugability of these frequently unstable and rapidly cleared molecules, chemical modifications are of great interest. Automated solid-phase peptide synthesis (SPPS) offers a suitable technology to produce chemically...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077397
PubMed Central
by Geffe, Mario; Andernach, Lars; Trapp, Oliver; Opatz, Till
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999880
PubMed Central
by Koszytkowska-Stawinska, Mariola; Buchowicz, Wlodzimierz
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract This review covers sixty original publications dealing with the application of multicomponent reactions (MCRs) in the synthesis of novel nucleoside analogs. The reported approaches were employed for modifications of the parent nucleoside core or for de novo construction of a nucleoside scaffold from non-nucleoside substrates. The cited references are grouped according to the usually recognized types of the MCRs....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142899
PubMed Central
by Yamabe, Shinichi; Zeng, Guixiang; Guan, Wei; Sakaki, Shigeyoshi
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Wolff–Kishner reduction reactions were investigated by DFT calculations for the first time. B3LYP/6-311+G(d,p) SCRF=(PCM, solvent = 1,2-ethanediol) optimizations were carried out. To investigate the role of the base catalyst, the base-free reaction was examined by the use of acetone, hydrazine (H2N–NH2) and (H2O)8. A ready reaction channel of acetone → acetone hydrazine (Me2C=N–NH2) was obtained. The...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943666
PubMed Central
by Rackl, Daniel; Kais, Viktor; Kreitmeier, Peter; Reiser, Oliver
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168922
PubMed Central
by Willms, J Alexander; Beel, Rita; Schmidt, Martin L; Mundt, Christian; Engeser, Marianne
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A new 4-hydroxy-L-proline derivative with a charged 1-ethylpyridinium-4-phenoxy substituent has been synthesized with the aim of facilitating mechanistic studies of proline-catalyzed reactions by ESI mass spectrometry. The charged residue ensures a strongly enhanced ESI response compared to neutral unmodified proline. The connection by a rigid linker fixes the position of the charge tag far away from the...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168921
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract 2-Hydroxy-4-pentynoic acid (1) is a key intermediate towards ‘clickable’ polylactide which allows for efficient introduction of a broad range of pendant functional groups onto polymers from a single monomer via convenient ‘click’ chemistry with organic azides. The incorporation of various pendant functional groups could effectively tailor the physicochemical properties of polylactide. The reported...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077406
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077373
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl)propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2-iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077525
PubMed Central
by Koopmanschap, Gijs; Ruijter, Eelco; Orru, Romano VA
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract In the recent past, the design and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the flexibility of the peptide enhancing often affinity for a certain receptor....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943360
PubMed Central
by Mari, Michele; Lucarini, Simone; Bartoccini, Francesca; Piersanti, Giovanni; Spadoni, Gilberto
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168769
PubMed Central
by Tomita, Ren; Yasu, Yusuke; Koike, Takashi; Akita, Munetaka
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Background: Trifluoromethylated alkene scaffolds are known as useful structural motifs in pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit limitation with respect to access to tri- and tetrasubstituted CF3-alkenes. Thus development of new methodologies for facile construction of Calkenyl–CF3 bonds is...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077392
PubMed Central
by Elschner, Thomas; Heinze, Thomas
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A novel polyzwitterion possessing weak ionic groups could be efficiently synthesized from cellulose phenyl carbonate. Polyanion, polycation, and polyzwitterion are accessible by orthogonal removal of protecting groups. The molecular structure was proofed by FTIR- and NMR spectroscopy. Characteristic properties of the cellulose derivatives, e.g., acid dissociation constants, isoelectric point and complexation,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142972
PubMed Central
by Nieto, Carla I; Cabildo, Pilar; Garcia, M Angeles; Claramunt, Rosa M; Alkorta, Ibon; Elguero, Jose
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract This paper reports the 1H, 13C and 15N NMR experimental study of five benzimidazoles in solution and in the solid state (13C and 15N CPMAS NMR) as well as the theoretically calculated (GIAO/DFT) chemical shifts. We have assigned unambiguously the "tautomeric positions" (C3a/C7a, C4/C7 and C5/C6) of NH-benzimidazoles that, in some solvents and in the solid state, appear different (blocked tautomerism)....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142846
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A highly regioselective SN2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents the first direct transformation of MBH alcohols into hydrazines.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077529
PubMed Central
by Peach, Jocelyn; Eastoe, Julian
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Supercritical carbon dioxide (scCO2) could be one aspect of a significant and necessary movement towards green chemistry, being a potential replacement for volatile organic compounds (VOCs). Unfortunately, carbon dioxide has a notoriously poor solubilising power and is famously difficult to handle. This review examines attempts and breakthroughs in enhancing the physicochemical properties of carbon dioxide,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168859
PubMed Central
by Hanson, Paul R
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract None
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168958
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Pyrrolo[2,1-a]isoquinoline alkaloids have been prepared via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization cascade using Rose Bengal as an organo-photocatalyst. A variety of pyrroloisoquinolines have been obtained in good yields under mild and metal-free reaction conditions.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077507
PubMed Central
by Telle, Werner; Kelter, Gerhard; Fiebig, Heinz-Herbert; Jones, Peter G; Lindel, Thomas
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The marine natural product malevamide D from the cyanobacterium Symploca hydnoides was synthesized for the first time. The final peptide coupling linked the dolaisoleuine and dolaproine subunits. The phenyl group of malevamide D was also functionalized with a photoreactive diazirine moiety, which was carried through seven reaction steps. Comprehensive assessment of the cytotoxicity in a panel of 42 human cancer...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943603
PubMed Central
by Lakshman, Mahesh K; Singh, Manish K; Kumar, Mukesh; Chamala, Raghu Ram; Yedulla, Vijayender R; Wagner, Domenick; Leung, Evan; Yang, Lijia; Matin, Asha; Ahmad, Sadia
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract (1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4-methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168895
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Over the past 20 years, the generation of functional RNAs by in vitro selection has become a standard technique. Apart from aptamers for simple binding of defined ligands, also RNAs for catalysis of chemical reactions have been selected. In the latter case, a key step often is the conjugation of one of the two reactants to the library, requiring suitable strategies for terminal or internal RNA functionalization....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168874
PubMed Central
by Pawar, Nitin J; Sidhu, Navdeep S; Sheldrick, George M; Dhavale, Dilip D; Diederichsen, Ulf
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Carbohydrate recognition is essential in cellular interactions and biological processes. It is characterized by structural diversity, multivalency and cooperative effects. To evaluate carbohydrate interaction and recognition, the structurally defined attachment of sugar units to a rigid template is highly desired. β-Peptide helices offer conformationally stable templates for the linear presentation of sugar...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077383
PubMed Central
by Majek, Michal; Filace, Fabiana; von Wangelin, Axel Jacobi
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A combined spectroscopic, synthetic, and apparative study has allowed a more detailed mechanistic rationalization of several recently reported eosin Y-catalyzed aromatic substitutions at arenediazonium salts. The operation of rapid acid–base equilibria, direct photolysis pathways, and radical chain reactions has been discussed on the basis of pH, solvent polarity, lamp type, absorption properties, and quantum...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077370
PubMed Central
by Griesbeck, Axel G
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract None
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077364
PubMed Central
by Reinelt, Sebastian; Tabatabai, Monir; Fischer, Urs Karl; Moszner, Norbert; Utterodt, Andreas; Ritter, Helmut
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Thiol–ene photopolymerizations gain a growing interest in academic research. Coatings and dental restoratives are interesting applications for thiol–ene photopolymerizations due to their unique features. In most studies the relative flexible and hydrophilic ester derivative, namely pentaerythritoltetra(3-mercaptopropionate) (PETMP), is investigated as the thiol component. Thus, in the present study we are...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142978
PubMed Central
by Rabe, Patrick; Klapschinski, Tim A; Brock, Nelson L; Citron, Christian A; D'Alvise, Paul; Gram, Lone; Dickschat, Jeroen S
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure–activity relationship (SAR) study, revealing that the sulfur-free...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142847
PubMed Central
by Chakraborty, Sourav; Mondal, Snehasish; Kumari, Rina; Bhowmick, Sourav; Das, Prolay; Das, Neeladri
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A facile and efficient synthesis of a new series of triptycene-based tripods is being reported. Using 2,6,14- or 2,7,14-triaminotriptycenes as synthons, the corresponding triazidotriptycenes were prepared in high yield. Additionally, we report the transformation of 2,6,14- or 2,7,14-triaminotriptycenes to the corresponding ethynyl-substituted triptycenes via their tribromo derivatives. Subsequently,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077457
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The synthesis of (diarylmethyl)sulfonamides and related compounds by a new manganese-mediated, cobalt-catalyzed three-component reaction between sulfonamides, carbonyl compounds and organic bromides is described. This organometallic Mannich-like process allows the formation of the coupling products within minutes at room temperature. A possible mechanism, emphasizing the crucial role of manganese is proposed.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3944212
PubMed Central
by Ghobrial, Michael; Mihovilovic, Marko D; Schnurch, Michael
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C–H and N–H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168884
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract This review highlights the state of the art in the field of continuous flow nitration with miniaturized devices. Although nitration has been one of the oldest and most important unit reactions, the advent of miniaturized devices has paved the way for new opportunities to reconsider the conventional approach for exothermic and selectivity sensitive nitration reactions. Four different approaches to flow nitration...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943559
PubMed Central
by Levic, Jasmin; Micura, Ronald
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Pre-queuosine or queuine (preQ1) is a guanine derivative that is involved in the biosynthetic pathway of the hypermodified tRNA nucleoside queuosine (Que). The core structure of preQ1 is represented by 7-(aminomethyl)-7-deazaguanine (preQ1 base). Here, we report the synthesis of three preQ1 base derivatives with complementary 15N-labeling patterns, utilizing [15N]-KCN, [15N]-phthalimide, and [15N3]-guanidine as...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168690
PubMed Central
by Beltra, Jorge; Gimeno, M Concepcion; Herrera, Raquel P
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A novel approach for the catalyzed formation of bisindolylmethane derivatives (BIMs) is described. This methodology is the unique example where AgOTf has been successfully used for the activation of aldehydes, giving easy access to a broad range of bisindolyl derivatives with excellent results. Moreover, the simplicity and easy operational methodology using a small amount of commercially available AgOTf (1–3...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168942
PubMed Central
by Fateev, Ilja V; Antonov, Konstantin V; Konstantinova, Irina D; Muravyova, Tatyana I; Seela, Frank; Esipov, Roman S; Miroshnikov, Anatoly I; Mikhailopulo, Igor A
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Two approaches to the synthesis of 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (1, clofarabine) were studied. The first approach consists in the chemical synthesis of 2-deoxy-2-fluoro-α-D-arabinofuranose-1-phosphate (12a, 2FAra-1P) via three step conversion of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (9) into the phosphate 12a without isolation of intermediary products....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142866
PubMed Central
by Feast, George C; Lepitre, Thomas; Mulet, Xavier; Conn, Charlotte E; Hutt, Oliver E; Savage, G Paul; Drummond, Calum J
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142986
PubMed Central
by Lesma, Giordano; Meneghetti, Fiorella; Sacchetti, Alessandro; Stucchi, Mattia; Silvani, Alessandra
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077467
PubMed Central
by Patil, Vilas Venunath; Shankarling, Ganapati Subray
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A new protocol for the oxidative bromination of aminoanthracene-9,10-dione, which is highly deactivated towards the electrophilic substitution is investigated. The peracid, nonanebis(peroxoic acid), possesses advantages such as better stability at room temperature, it is easy to prepare and non-shock sensitiv as compared to the conventional peracids. The present protocol has a broad scope for the bromination of...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077418
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The intramolecular C–H insertion of the Mes*-substituted phosphanylidenecarbene [Mes*P=C:] (Mes* = 2,4,6-t-Bu3C6H2) and physicochemical properties of the cyclized product, 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene were studied based on ab initio calculations. Whereas the alternative Fritsch–Buttenberg–Wiechell-type rearrangement requires almost no activation energy, the intramolecular...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077427
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract New compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943604
PubMed Central
by Lindhorst, Thisbe K; Elsner, Katharina
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Glycodendrons are multivalent glycoconjugates bearing an orthogonal functional group at the focal point of the molecule. This allows for their postsynthetic elaboration to achieve amphiphilic glycolipid mimetics, for example, which eventually can be applied in biology, biophysics, or material science. Here, postsynthetic modification of di- and tetravalent polyether glycodendrons has been explored using...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142895
PubMed Central
by Lepage, Mathieu L; Meli, Alessandra; Bodlenner, Anne; Tarnus, Celine; De Riccardis, Francesco; Izzo, Irene; Compain, Philippe
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide–alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077385
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chiral cyclopentane-1,2-diol and -1,2,3-triol derivatives. This unusual substitution pattern provides a useful starting...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077357
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Heterogeneous polymer-supported triphenylphosphine oxides based on the rasta resin architecture have been synthesized, and applied as reagent precursors in a wide range of halogenation reactions. The rasta resin–triphenylphosphine oxides were reacted with either oxalyl chloride or oxalyl bromide to form the corresponding halophosphonium salts, and these in turn were reacted with alcohols, aldehydes, aziridines...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077539
PubMed Central
by Zapol'skii, Viktor A; Namyslo, Jan C; Gjikaj, Mimoza; Kaufmann, Dieter E
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene (1) provides an appropriate precursor for the synthesis of special thiazolidin-4-ones. Applying different anilines as the second constituent for the requisite cyclization step, a series of (Z)-2-allylidenethiazolidin-4-ones was obtained in yields up to 81%. Some subsequent reactions have been examined too, such as the formation of...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142838
PubMed Central
by Harmrolfs, Kirsten; Mancuso, Lena; Drung, Binia; Sasse, Florenz; Kirschning, Andreas
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The preparation of alkyne-modified ansamitocins by mutasynthetic supplementation of Actinosynnema pretiosum mutants with alkyne-substituted aminobenzoic acids is described. This modification paved the way to introduce a thiol linker by Huisgen-type cycloaddition which can principally be utilized to create tumor targeting conjugates. In bioactivity tests, only those new ansamitocin derivatives showed strong...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943755
PubMed Central
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077384
PubMed Central
by Gangadhararao, G; Kotikalapudi, Ramesh; Nagarjuna Reddy, M; Swamy, K C Kumara
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077435
PubMed Central
by Smadhi, Meriem; de Bentzmann, Sophie; Imberty, Anne; Gingras, Marc; Abderrahim, Raoudha; Goekjian, Peter G
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Readily accessible, low-valency glycoclusters based on a triazine core bearing D-galactose and L-fucose epitopes are able to inhibit biofilm formation by Pseudomonas aeruginosa. These multivalent ligands are simple to synthesize, are highly soluble, and can be either homofunctional or heterofunctional. The galactose-decorated cluster shows good affinity for Pseudomonas aeruginosa lectin lecA. They are convenient...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168900
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization–endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077508
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by Kostyuchenko, Anastasia S; L.Yurpalov, Vyacheslav; Kurowska, Aleksandra; Domagala, Wojciech; Pron, Adam; Fisyuk, Alexander S
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A new synthetic approach towards the preparation of functionalised, soluble, donor–acceptor (DA) alkylbithiophene derivatives of oxadiazole, thiadiazole and triazole is reported. Taking advantage of the Fiesselmann reaction, reactive bithiophene synthons having alkyl or alkoxy substituents at designated positions are prepared. Following a synthetic strategy, featuring the bottom-up approach, sequential...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142979
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by Fiore, Michele; Daskhan, Gour Chand; Thomas, Baptiste; Renaudet, Olivier
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract We describe the first one-pot orthogonal strategy to prepare well-defined cyclopeptide-based heteroglycoclusters (hGCs) from glycosyl thiols. Both thiol–chloroactetyl coupling (TCC) and thiol–ene coupling (TEC) have been used to decorate cyclopeptides regioselectively with diverse combination of sugars. We demonstrate that the reaction sequence starting with TCC can be performed one-pot whereas the reverse...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142873
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselective Pd-catalysed cyclisation of...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168889
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by Krueger, Anke
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract None
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142960
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by Kim, Keunsoo; Punna, Venkateshwarlu; Karri, Phaneendrasai; Krishnamurthy, Ramanarayanan
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract IsoGNA, an isomer of glycerol nucleic acid GNA, is a flexible (acyclic) nucleic acid with bases directly attached to its linear backbone. IsoGNA exhibits (limited) base-pairing properties which are unique compared to other known flexible nucleic acids. Herein, we report on the details of the preparation of isoGNA phosphoramidites and an alternative route for the synthesis of the adenine derivative. The synthetic...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168771
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by Khlebnikov, Alexander F; Novikov, Mikhail S; Gorbunova, Yelizaveta G; Galenko, Ekaterina E; Mikhailov, Kirill I; Pakalnis, Viktoriia V; Avdontceva, Margarita S
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Theoretical and experimental studies of the reaction of isoxazoles with diazo compounds show that the formation of 2H-1,3-oxazines proceeds via the formation of (3Z)-1-oxa-5-azahexa-1,3,5-trienes which undergo a 6π-cyclization. The stationary points corresponding to the probable reaction intermediates, isoxazolium N-ylides, were located by DFT calculations at the B3LYP/6-31G(d) level only for derivatives without...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168923
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by Pakulski, Zbigniew; Gajda, Norbert; Jawiczuk, Magdalena; Frelek, Jadwiga; Cmoch, Piotr; Jarosz, Slawomir
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077423
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by Oku, Naoya; Matsumoto, Miyako; Yonejima, Kohsuke; Tansei, Keijiroh; Igarashi, Yasuhiro
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Macroscopic gelatinous colonies of freshwater cyanobacterium Aphanothece sacrum, a luxury ingredient for Japanese cuisine, were found to contain a new oxylipin-derived macrolide, sacrolide A (1), as an antimicrobial component. The configuration of two chiral centers in 1 was determined by a combination of chiral anisotropy analysis and conformational analysis of different ring-opened derivatives. Compound 1...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142850
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by Ley, Christian; Christmann, Julien; Ibrahim, Ahmad; Stefano, Luciano H Di; Allonas, Xavier
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The combination of a dye which absorbs the photon, an electron acceptor and an electron donor leading to energy conversion through electron transfer, was the basis of the so called three-component systems. In this paper, an experimental work combining Rose bengal dye with a triazine derivative as electron acceptor and ethyl 4-(dimethylamino)benzoate as electron donor, will underline the benefit of the photocyclic...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077436
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by Rauschenberg, Melanie; Fritz, Eva-Corrina; Schulz, Christian; Kaufmann, Tobias; Ravoo, Bart Jan
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The molecular recognition of carbohydrates and proteins mediates a wide range of physiological processes and the development of synthetic carbohydrate receptors (“synthetic lectins”) constitutes a key advance in biomedical technology. In this article we report a synthetic lectin that selectively binds to carbohydrates immobilized in a molecular monolayer. Inspired by our previous work, we prepared a...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077543
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by Farcas, Aurica; Resmerita, Ana-Maria; Aubert, Pierre-Henri; Farcas, Flavian; Stoica, Iuliana; Airinei, Anton
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract We report on the synthesis as well as the optical, electrochemical and morphological properties of two polyrotaxanes (4a and 4b), which consist of electron-accepting 9,9-dicyanomethylenefluorene 1 as an inclusion complex in persilylated β- or γ-cyclodextrin (TMS-β-CD, TMS-γ-CD) (1a, 1b) and methyltriphenylamine as an electron-donating molecule. They are statistically distributed into the conjugated chains of...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168896
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by Rose, Bradley D; Santa Maria, Peter J; Fix, Aaron G; Vonnegut, Chris L; Zakharov, Lev N; Parkin, Sean R; Haley, Michael M
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168888
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by Hopf, Henning; Narayanan, Swaminathan Vijay; Jones, Peter G
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Under basic conditions 4,5,12,13-tetraacetyl[2.2]paracyclophane (9) cyclizes by a double aldol condensation to provide the two aldols 12 and 15 in a 3:7 ratio. The structures of these compounds were obtained from X-ray structural analysis, spectroscopic data, and mechanistic considerations. On acid treatment 12 is dehydrated to a mixture of the condensed five-membered [2.2]paracyclophane derivatives 18–20,...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168897
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by Albler, Christopher; Hollaus, Ralph; Kahlig, Hanspeter; Schmid, Walther
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Higher aminosugars are interesting targets in carbohydrate synthesis since these compounds play important roles in biological systems. However, their availability from natural sources is limited. Thus, in order to investigate their biological function, the development of facile and adaptable routes to this class of compounds is of fundamental importance. Our synthetic route towards these target molecules makes...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168925
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles. The obtained C-allyl glycoside has been utilized for the synthesis of a orthogonally protected...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943741
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by Fadel, Salah; Hajbi, Youssef; Khouili, Mostafa; Lazar, Said; Suzenet, Franck; Guillaumet, Gerald
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943289
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by Burns, Michael J; Ronson, Thomas O; Taylor, Richard J K; Fairlamb, Ian J S
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077367
This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Highly efficient CO2 absorption was realized through formation of zwitterionic adducts, combining synthetic strategies to ionic liquids (ILs) and coordination. The essence of our strategy is to make use of multidentate cation coordination between Li+ and an organic base. Also PEG-functionalized organic bases were employed to enhance the CO2-philicity. The ILs were reacted with CO2 to form the zwitterionic adduct....
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168910
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Isosorbide was esterified with acryloyl chloride and crotonic acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Poly(isosorbide itaconite -co- succinate) 13 as a bio-based unsaturated polyester was cross-linked by a 1,3-dipolar...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077400
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by Silla, Josue M; Duarte, Claudimar J; Cormanich, Rodrigo A; Rittner, Roberto; Freitas, Matheus P
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract The gauche effect in fluorinated alkylammonium salts is well known and attributed either to an intramolecular hydrogen bond or to an electrostatic attraction between the positively charged nitrogen and the vicinal electronegative fluorine atom. This work reports the effect of adding a fluorine atom in 2-fluoroethylamine hydrochloride on the conformational isomerism of the resulting 2,2-difluoroethylamine chloride...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999868
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by Duan, Zhiqiang; Han, Jianlin; Qian, Ping; Zhang, Zirui; Wang, Yi; Pan, Yi
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract We show a convenient decarboxylative aldol process using a scandium catalyst and a PYBOX ligand to generate a series of highly functionalized chiral α-hydroxy esters. The protocol tolerates a broad range of β-keto acids with inactivated aromatic and aliphatic α-keto esters. The possible mechanism is rationalized.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077541
PubMed Central
by Yotapan, Nattawut; Charoenpakdee, Chayan; Wathanathavorn, Pawinee; Ditmangklo, Boonsong; Wagenknecht, Hans-Achim; Vilaivan, Tirayut
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract DNA or its analogues with an environment-sensitive fluorescent label are potentially useful as a probe for studying the structure and dynamics of nucleic acids. In this work, pyrrolidinyl peptide nucleic acid (acpcPNA) was labeled at its backbone with Nile red, a solvatochromic benzophenoxazine dye, by means of click chemistry. The optical properties of the Nile red-labeled acpcPNA were investigated by UV–vis...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168962
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by Bruss, Hanna; Schuster, Hannah; Martinez, Remi; Kaiser, Markus; Antonchick, Andrey P; Waldmann, Herbert
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943702
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by Kretschmer, Claudia; Dittmann, Gertrud; Beck, Johannes
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Two macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142877
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by Tarabova, Denisa; Soralova, Stanislava; Breza, Martin; Fronc, Marek; Holzer, Wolfgang; Milata, Viktor
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Activated enol ethers derived from esters or the dinitrile of malonic acid, or from pentane-2,4-dione were treated with hydrazine hydrate. The structures of the obtained products – pyrazoles 5 – were studied with a focus on tautomerism and supramolecular structure. A reverse addition of the reagents led to the isolation of two novel products, namely bis-enehydrazines 6 with an unsymmetrical arrangement of the...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999851
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by Nguyen, Theresa H; Maity, Soumitra; Zheng, Nan
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract Intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes is realized using visible light photoredox catalysis, yielding a variety of cyclic allylic amines in fair to good yields. This method exhibits significant group tolerance particularly with heterocycles. It can also be used to prepare complex heterocycles such as fused indolines.
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077375
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by Senadheera, Sanjeewa N; Yousef, Abraham L; Givens, Richard S
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This article is from Beilstein Journal of Organic Chemistry , volume 10 . Abstract We have developed a new photoremovable protecting group for caging phosphates in the near UV. Diethyl 2-(4-hydroxy-1-naphthyl)-2-oxoethyl phosphate (14a) quantitatively releases diethyl phosphate upon irradiation in aq MeOH or aq MeCN at 350 nm, with quantum efficiencies ranging from 0.021 to 0.067 depending on the solvent composition. The deprotection reactions originate from the triplet excited state, are...
Source: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168878