The preparation of Thiazolidine-2-thiones from N-alkylglucosylamines

Abstract

N-Alkylglucosylamines and carbon disulphide react to give 3-alkyl-5-hydroxy- 5-(D-arabino-tetrahydroxybutyl)thiazolidine-2-thiones (I), which dehydrate to the corresponding Δ⁴-thiazolines, isolated only as tetraacetates. A thiazolidine-2-thione forms also from the action of carbon disulphide on 1-N-methylamino-1-deoxy-D-fructose. l-Bromo-l-deoxy-2,3:4,5-di-O-isopropylidene-D-fructose is obtained by the action of dibromotriphenoxyphosphorane on 2,3:4,5-di-O-isopropylidene-D-fructose.