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. Copyright (C) 1996 Elsevier Science Ltd
Saladino, R., Mincione, E., Crestini, C., Mezzetti, M. (1996). Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane. TETRAHEDRON, 52(19), 6759-6780 [10.1016/0040-4020(96)00289-X].
Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane.
CRESTINI, CLAUDIA;MEZZETTI, MAURA
1996-01-01
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 formation of disulfides. Copyright (C) 1996 Elsevier Science LtdI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
