Heterocycles p. 2113 - 2125 (2015)
Update date:2022-08-17
Topics:
Cheng, Feng-Chang
Yin, Long
Liu, Wei-Wei
Li, Qu-Xiang
Tang, Li-Juan
Shi, Da-Hua
Cao, Zhi-Ling
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.
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Doi:10.1039/c7cy01834g
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