2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl) imino-1,3-thiazoline 유도체의 합성

Abstract

2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl)imino-1,3-thiazoline deri vatives 5 were synthesized from a reaction of N-methyl-N'-(β-D-glucopyranosyl)thiourea 3 with phenyl 4-chloroacetamide derivatives 4. N-methyl-N'-(β-D-glucopyranosyl)thiourea 3 was obtained by a dehydrochlorination of β-D-glucosamine hydrogenchloride salt 1 followed by the reaction of methyl isothiocyanate 2 of which structures were confirmed by their 1H NMR spectra. thus, the protons of 3-methyl, methylene,5- vinyl showed in range of δ 2.9-3.1 ppm, 4.6-4.7 ppm and 6.9-7.1 ppm respectvely without influence of functional group of the side stereochemistry of the compounds. The synthesized compounds would be contributed a chemical library for an exploration of new biological active material.