Synthesis of 4- C-(1-hydroxyethyl) derivatives from benzyl 2,3-di- O-benzyl- and -2,3- O-methylene-β- l- threo-pentopyranosid-4-ulose, and the corresponding α- d- xylo-hexopyranosid-4-uloses

Abstract

The title compounds were synthesized by the epoxidation of the corresponding 4- C-vinyl derivatives followed by reduction of the epoxy ring (Route A), and by osmium tetraoxide oxidation of the corresponding 4- C-ethylidene derivatives (Route C). Stereoselectivities in the oxidations are discussed on the basis of the chiralities of 1-hydroxyethyl groups as determined by comparison of the products prepared through Routes A and C.