Some 3,5-acetal derivatives of d-glucitol

Abstract

Ethylidenation of 1,6-di- O-benzoyl-2,4- O-benzylidene- d-glucitol gave the 3,5- O-ethylidene derivative in poor yield, whereas reaction with 2,2-dimethoxypropane gave the 3,5- O-isopropylidene derivative in good yield. Removal of the benzoyl and benzylidene groups, with further derivatisation, gave a variety of compounds containing the relatively unstable 3,5-acetal ring. Attempted tosylation of 3,5- O-isopropylidene- d-glucitol gave a derivative of 1,4-anhydro- d-glucitol. Reduction of various ditosylates revealed selective reaction of axial tosyloxymethyl groups.