Synthesis and reactions of chlorodeoxy-l-talofuranoid derivatives

Abstract

Reaction of 6-O-acyl-3,5-O-benzylidene derivatives of 1,2-O-isopropylidene-α-d-glucofuranose with N-bromosuccinimide affords mainly 5-O-acyl-6-bromo-6-deoxy-1,2-O-isopropylidene-β-l-idofuranose in good yield. Convenient preparative routes to 1,2-O-isopropylidene-β-l-talofuranose and its conversion into 5-chloro-5-deoxy and 5,6-dichloro-5,6-dideoxy derivatives are described. © 1990.