A Straightforward Diphenylmethyl Protection Method and Deprotection of Some Pyrimidine Nucleosides

Abstract

Benzhydryl protection of primary and secondary alcohols has been reported previously via reaction with metal alcoholates. Our aim was to find generally useful and very mild conditions for the alcoholic protection and deprotection of nucleosides with the diphenylmethyl group. This was accomplished for some pyrimidine nucleosides using PdCl2 as the transition metal catalyst, and with optimization yields of 70–90% have been achieved. A lack of solubility of other nucleosides hampers its more general use.

Keywords

• hydroxyl protecting group
• palladium catalyst
• nucleoside
• diphenyl methyl