A general method for controlling glycosylation stereochemistry in the synthesis of 2′-deoxyribose nucleosides

Article abstract of DOI:10.1016/S0040-4039(00)98793-8

Glycosylation reactions of 2-arylsulfinyl-O-acetylribosides6 with silylated thymine11 produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T,2, is described. Glycosylation reactions of 2-arylsulfinyl-O-acetylribosideswith silylated thymine produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T is described. (Chemical Equation Presented).