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

Abstract Thymidine ( 2 ) and 5-methyl-2′- O -( t -butyldimethylsilyl)uridine ( 3 ) deuterated at the C3′-position were prepared with complete stereocontrol via NaB 2 H 4 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.