On the Benzylation of Nucleosides. I. Reaction of Uridine with Benzyl Bromide in the Presence of Sodium Hydride

Abstract

Uridine was benzylated with benzyl bromide in the presence of sodium hydride in dimethyl sulfoxide or dimethylformamide to give two products. The one was a dibenzyl uridine (I), yield 33%, and the other N₃-benzyluridine (II), yield 30.5%. The product (I) was converted to the product (II) by catalytic hydrogenation and was identified with N₃, 2'-O-dibenzyluridine which was synthesized by detritylation of N₃, 2'-O-dibenzyl-3', 5'-di-O-trityluridine (IV) derived by the similar benzylation of the known 3', 5'-di-O-trityluridine (III).