文献类型：期刊文献

英文题名：A new synthesis of α-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate with hydroquinone

作者：Wang, Zhao-Xia; Shi, Xiao-Xin; Chen, Guo-Rong; Ren, Zhi-Hua; Luo, Lei; Yan, Jing

机构：[1]E China Univ Sci & Technol, Inst Fine Chem, Adv Mat Lab, Shanghai 200237, Peoples R China

年份：2006

卷号：341

期号：11

起止页码：1945

外文期刊名：CARBOHYDRATE RESEARCH

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000238797300020)，CCR-EXPANDED(收录号:WOS:000238797300020)】；

语种：英文

外文关键词：alpha-arbutin; trichloracetimidate; hydroquinone; glycosylation

摘要：alpha-Arbutin has huge application potentials in the cosmetic industry, as its inhibitory effect on human tyrosinase is stronger than that of its naturally occurring anomer arbutin (4-hydroxyphenyl P-D-glucopyranoside). Enzymatic synthesis was preferred for alpha-arbutin previously, and now a new chemical synthesis is reported. The reaction of tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate, as glycosyl donor, with hydroquinone was initiated by catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf). resulting in 4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside with high stereoselectivity and yield, and then to alpha-arbutin quantitatively after deprotection. (c) 2006 Elsevier Ltd. All rights reserved.