Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

DOI: 10.1016/0040-4020(96)00289-X

Source and publish data:

Tetrahedron p. 6759 - 6780 (1996)

Update date:2022-08-03

Topics:

Authors:

Saladino, Raffaele

Mincione, Enrico

Crestini, Claudia

Mezzetti, Maurizio

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Article abstract of DOI:10.1016/0040-4020(96)00289-X

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 formation of disulfides.

Full text of DOI:10.1016/0040-4020(96)00289-X

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