Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

Abstract

Synthesis of N 3,2′,3′-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5′-O-(2-deoxy-α-d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.