Stereoselective synthesis of 2',3'-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2',3'-dideoxythymidine

Article abstract of DOI:10.1016/S0040-4039(98)00093-8

4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lead to neutral β-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol.