A Synthesis of 2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl) imino-1,3-thiazoline Derivatives

Abstract

2-(1,3,4,6-tetra-0-acety1-2-deoxy-β-D-g1ucopyranosy1)imino-1,3-thiazo1ine deri vatives 5 were synthesized from a reaction ofN-methy1-N'-(β-D-g1ucopyranosy1)thiourea 3 with phenyl 4-ch1oroacetamide derivatives 4. N-methy1-N'-(β-D-g1ucopyranosy1)thiourea 3 was obtained by a dehydrochlormation of β-D-g1ucosamine hydrogenchloride salt 1 followed by the reaction ofmethyl isothiocyanate 2 of which structures were confirmed by their H NMR spectra, thus, the protons of3-methy1, methylene,5- vinyl showed in range of δ2.9-3.1 ppm, 4.6-4.7 ppm and 6.9-7.1 ppm respectvely without influence offunctional group oftheside stereochemistry ofthe compounds. The synthesized compounds would be contributed a chemical library for an explorationofnew biological active material.