The Treatment of Some Carbohydrate Alcohols and Diols With N-Dibromomethylene-N,N-Dialkylammonium Bromides: a Synthesis of Glycosyl Bromides

Abstract

Two analogues of Viehe's salt (Me₂N⁺=CCl₂Cl^-), namely Me₂N⁺=CBr₂ Br^- and Et₂N⁺=CBr₂ Br^-, were prepared and treated with various carbohydrate alcohols and diols. With the diols, the products formed corresponded to those previously obtained with Viehe's salt itself, namely bromo deoxy sugars, cyclic carbonates or carbamates, and depended on the nature of the substrate and the reaction conditions. With the alcohols, mainly free sugars, a useful synthesis of glycosyl bromides was achieved.