Chemical modification of trehalose. Part IX. The monobenzylidene acetal

Abstract

Selective acid-catalysed methanolysis of 4,6:4′,6′-di-O-benzylidene-αα-trehalose tetrabenzoate afforded, after chromatography, a 47% yield of 2,3-di-O-benzoyl-α-D-glucopyranosyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside. Debenzoylation gave 4,6-O-benzylidene-αα-trehalose, which has been characterised as several ester derivatives. Extensive use has been made of ¹H n.m.r. spectroscopy for the structural elucidation of these products.