An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogenoacetates

Publisher Website
Google Scholar
Abstract
A three-step reaction sequence starting from a ribonucleoside to give the corresponding 5′-O-acyl-2′,3′-didehydro-2′,3′-dideoxynucleoside is described. The key intermediate is the bromoacetate, made by reaction of the 2′,3′-methoxyethylidene nucleoside with acetyl bromide. Reductive elimination of the bromoacetate using a zinc-copper couple furnishes the desired compounds in good overall yield.

This publication has 0 references indexed in Scilit: