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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


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.