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Paper | Regular issue | Vol 91, No. 11, 2015, pp.2113-2125
Published online, 8th October, 2015
DOI: 10.3987/COM-15-13310
Expedient Synthesis of Novel Glycosyl Thiazole Derivatives

Feng-chang Cheng, Long Yin, Wei-wei Liu,* Qu-xiang Li, Li-juan Tang, Da-hua Shi, and Zhi-ling Cao

*School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang City, Jiangsu Province 222005, China

Abstract

An efficient protocol for the synthesis of novel glycosyl thiazole derivatives starting from the commercially available D-glucosamine hydrochloride was described by reaction of 1-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea 8 with each of substituted α-bromoacetophenone in ethanol. 1-(1,3,4,6-Tetra-O-benzyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea was an important intermediate, and its synthetic methods were discussed by comparing two different synthetic routes. Moreover, 2-isothiocyanate-1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranose was obtained in a new and convenient way. Finally, a series of novel glycosyl incorporated with thiazole moiety was synthesized in good purities and overall yields.