Synthesis and characterisation a new 1,2,4-triazole carbohydrate

Abstract

In this study, new alditol derivatives containing two triazole rings at the two terminal primary carbon atoms have synthesized starting from D-glucitol. In order to obtain these derivatives, it was required to protect the hydroxyl group at C1 and C6 position of the glucitol by converting them to 1,6-di-O-benzoyl-D-glucitol, followed by the protection of the remaining hydroxyl group. Treatment of 1,6-di-O-benzoyl-D-glucitol with benzaldehyde in present of zinc chloride as catalyst afforded 1,6-di-O-benzoyl-2,4:3,5-di-O-benzylidene, then the two benzoate groups were removed using sodium methoxide to give 2,4:3,5-di-O-benzylidene-D-glucitol. Oxidation of 2,4:3,5-di-O-benzylidene-D-glucitol with alkaline permanganate gave 1,4:3,5-di-O-benzylidene-D-glucaric acid. This was converted to corresponding acid chloride using thionyl chloride, and then treated with semicarbazide to afford the semicarbazide derivative.This undergoes intramolecular cyclization with base to give the triazolyl derivative. All derivatives were confirmed with the help of infrared spectra (IR), and nuclear magnetic resonance for proton 1HNMR and carbon13CNMR spectroscopy.