A Novel and Convenient Synthesis of Thiazol-2(3<i>H</i>)-imine-Linked Glycoconjugates

Abstract

A novel and convenient synthetic approach for the preparation of thiazol-2(3H)-imine-linked glycoconjugates, which involves the cyclization of 1-benzoyl-3-(2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranosyl)thiourea with a variety of carbonyl compounds bearing an α-H in the presence of [hydroxy(tosyloxy)iodo]benzene (HTIB) and triethylamine, has been developed. The methodology has advantages such as avoiding the use of lachrymatory and toxic bromine, simplicity of procedure, mild reaction conditions, and high yields.