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

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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).