Tetrahedron

Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

R Saladino, E Mincione, C Crestini, M Mezzetti

Index: Saladino, Raffaele; Mincione, Enrico; Crestini, Claudia; Mezzetti, Maurizio Tetrahedron, 1996 , vol. 52, # 19 p. 6759 - 6780

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Citation Number: 28

Abstract

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or ...

~88%

~90%

~80%

~84%

~93%

~86%

~81%

~93%

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