- Microwave assisted high yielding preparation of N-protected 2′-deoxyribonucleosides useful for oligonucleotide synthesis
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A rapid and high yielding method for the synthesis of precursors of synthons for DNA synthesis, N-protected 2′-deoxyribonucleosides is described, which occur under mild conditions using microwave irradiation. The desired material, N-protected nucleosides, was obtained in 93-96% yield in few minutes. The final products were then characterized by H-NMR and MALDI-TOF and compared with the standard samples. The method is amenable to small to moderate scale of synthesis.
- Rao,Kumar,Chauhan,Garg,Gupta
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- A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor
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Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
- Liu, Guang-Jian,Zhang, Xiao-Tai,Xing, Guo-Wen
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p. 12803 - 12806
(2015/08/06)
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- Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters
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(Chemical Equation Presented) N,O-Peracylated cytidine and 2′-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125°C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.
- Nowak, Ireneusz,Robins, Morris J.
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p. 4903 - 4905
(2007/10/03)
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- 'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
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Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.
- Prasad, Ashok K.,Kumar, Vineet,Malhotra, Shashwat,Ravikumar, Vasulinga T.,Sanghvi, Yogesh S.,Parmar, Virinder S.
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p. 4467 - 4472
(2007/10/03)
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- Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides
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Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.
- Prasad, Ashok K.,Kumar, Vineet,Maity, Jyotirmoy,Wang, Zhiwei,Ravikumar, Vasulinga T.,Sanghvi, Yogesh S.,Parmar, Virinder S.
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p. 935 - 945
(2007/10/03)
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- Mild, efficient, selective and "green" benzoylation of nucleosides using benzoyl cyanide in ionic liquid
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Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3- methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2′-deoxy- and the ribo-series at ambient temperature was accomplished. Copyright Taylor & Francis, Inc.
- Prasad, Ashok K.,Kumar, Vineet,Maity, Jyotirmoy,Sanghvi, Yogesh S.,Ravikumar, Vasulinga T.,Parmar, Virinder S.
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p. 747 - 751
(2007/10/03)
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- Simplified Liquid-Phase Preparation of Four Decadeoxyribonucleotides and their Preliminary Spectroscopic Characterization
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Four self-complementary decadeoxyribonucleotides, dApTpApTpApTpApTpApT,dApTpApTpCpGpApTpApT, dApTpApTpGpCpApTpApT and dApApApApApTpTpTpTpT, were chemically synthesized by the phosphotriester procedure.Efforts were concentrated on keeping the procedure as simple as possible, concomitant with obtaining high-purity products at each step of the process.The decamers were elaborated from the 3'-end, starting with a 3'-O-benzoylated monomer according to the scheme: monomer + monomer -> dimer + dimer -> tetramer + dimer -> hexamer + tetramer -> decamer.Putity of intermediates and of the fully blocked decamers were monitored by chromatography and by 300-MHz 1H-NMR. spectroscopy.The deblocked decadeoxyribonucleotides were characterized by their UV., CD., and 1H-NMR. spectra.
- Denny, William A.,Leupin, Werner,Kearns, David R.
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p. 2372 - 2393
(2007/10/02)
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- N-ACYL PROTECTING GROUPS FOR DEOXYNUCLEOTSIDES A QUANTITATIVE AND COMPARATIVE STUDY
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A detailed study in search for suitable N-acyldeoxy-nucleosides which could serve as building blocks for the stepwise synthesis of deoxyoligonucleotides was undertaken.Several acyl groups namely 4-t-butylphenylacetyl, 4-t-butylphenoxyacetyl, 4-chlorobenzoyl, 3,4-dichlorobenzoyl, 2-methyl-benzoyl, 2,4-dimethylbenzoyl, nicotinoyl, 4-t-butylbenzoyl and 4-phenylazobenzoyl have been used for the protection of the exocyclic amino groups of deoxynucleosides.Interesting data concerning the stability of N-acyl groups towards a potent deacylating system (0.2N NaOH/MeOH) are presented.
- Koester, Hubert,Kulikowski, Konrad,Liese, Thomas,Heikens, Wiebke,Kohli, Vipin
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p. 363 - 369
(2007/10/02)
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