Synthesis of 4′,4′-C-diaminomethyl nucleoside derivative as a building block for constructing libraries via amide bond formation

Preparation of the 4′,4′-C-diaminomethyl uridine analog starting from the commercial uridine via 4′,4′-C-dihydroxymethyl uridine, 4′,4′-C-bis-trifluoromethanesulfonyloxymethyl uridine, and 4′,4′-C-diazidomethyl uridine in total eight steps was achieved in 8% yield. Steric hindrance between 3′-O-TBDMS and 5′-O-triflate prevented the undesired ring closure which made the synthesis of target compound feasible.