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.