Use of dimethoxydiphenylsilane, NN-dimethylformamide, and toluene-p-sulphonic acid as a novel acetalating reagent

Abstract

Reaction of sucrose with a combination of dimethoxydiphenylsilane, NN-dimethylformamide, and toluene-p-sulphonic acid gave a mixture of 1′,2-O-(diphenylsilylene)sucrose and 1′,2 : 6,6′-di-O(diphenylsilylene) sucrose, from which the 1′,2-silylene acetal has been isolated directly as its hexa-acetate (1) in 18% yield; the 1′,2 : 6,6′-disilylene acetal tetra-acetate (2) has been isolated after column chromatography.