PARTIALLY PROTECTED D-GLUCOPYRANOSYL ISOTHIOCYANATES - SYNTHESIS AND TRANSFORMATIONS INTO THIOUREA AND HETEROCYCLIC-DERIVATIVES

The syntheses of 2,3,4-tri-O-acetyl(benzoyl)-beta-D-glucopyranosyl isothiocyanates (3, 4) from the corresponding acylated N-(2,2-diethoxycarbonylvinyl)-beta-D-glucopyranosylamine are described. Reactions Of 3 and 4 with phenacylamine hydrochloride yielded N-phenacyl-N'-(2,3,4-tri-O-acyl-beta-D-glucopyranosyl)thioureas (6, 7) whereas treatments of the same compounds with aminoacetone hydrochloride gave the N-nucleoside analogues 5-methyl-1-(2',3',4-tri-O-acyl-beta-D-glucopyranosyl)4-imidazoline-2-thiones (8, 9). The partially protected N-(2-thiazolin-2-yl)-beta-D-glucopyranosylamine (10) and the thioureylenedisaccharide 11 were prepared from 4 and 2-chloroethylamine hydrochloride under different reaction conditions.