Electrophilic addition to 4-thio furanoid glycal: A highly stereoselective entry to 2'-deoxy-44'-thio pyrimidine nucleosides

Article abstract of DOI:10.1016/S0040-4039(98)00543-7

4-Thio furanoid glycals with different types of O-silyl protection have been prepared from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro- pentofuranoside. Face-selectivity for PhSeCl- or N-iodosuccimide-initiated addition of a pyrimidine base to the thioglycal protected with a 3,5-O-di-r- butylsilyl group, a highly stereoselective synthesis of β-2'-deoxy-4'-thio pyrimidine nucleoside has been accomplished.