Synthesis of 3'-deuterated pyrimidine nucleosides via stereoselective reduction of a protected 3-oxoribose

Article abstract of DOI:10.1016/S0040-4039(97)10815-2

Thymidine (2) and 5-methyl-2'-O-(t-butyldimethylsilyl)uridine (3) deuterated at the C3'-position were prepared with complete stereocontrol via NaB²H₄ reduction of a 3-oxoribose derivative (5). Utilization of benzyl protecting groups in the deuterated glycosidation substrate facilitates the synthesis of ribonucleosides and 2'-deoxyribonucleosides with minimal protecting group manipulations.