- '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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- A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates
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A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.
- Iimori, Takamasa,Kobayashi, Hiroshi,Hashimoto, Shun-Ichi,Ikegami, Shiro
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p. 485 - 488
(2007/10/03)
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- Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
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2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.
- Baud,Chavis,Lucas,Imbach
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p. 4437 - 4440
(2007/10/02)
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- SELECTIVE N-DEACYLATION OF N,O-PROTECTED NUCLEOSIDES BY ZINC BROMIDE
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N-Acyl protecting group in nucleoside derivatives can be selectively removed by treatment with zinc bromide in the presence of alcohols to give O-protected nucleosides.
- Kierzek, R.,Ito, H.,Bhatt, R.,Itakura, K.
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p. 3761 - 3764
(2007/10/02)
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