Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2', 3'-Anhydro, 2'(and 3')-Deoxy, 2', 3'-Didehydro-2', 3'-dideoxy, and 2', 3'- …

…, JS Wilson, D Madej, NH Low, F Hansske…

Index: Robins, Morris J.; Wilson, John, S.; Madej, Danuta; Low, Nicholas H.; Hansske, Fritz; Wnuk, Stanislaw F. Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7902 - 7908

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Citation Number: 37

Abstract

Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2- acetoxy-2-methylpropanoyl (a-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2', 3'-bromohydrin acetates with different 05 'substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2 ', 3'-0- isopropylidene derivatives as minor byproducts was detected for the first time. Acid- ...