NOVEL SYNTHESIS OF ARYL 2,3,4,6-TETRA-O-ACETYL-D-GLUCOPYRANOSIDES

被引：56

作者：

YAMAGUCHI, M

HORIGUCHI, A

FUKUDA, A

MINAMI, T

机构：

[1] Department of Applied Chemistry, Kyushu Institute of Technology, Tobata, Kitakyushu 804, Sensui-cho

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 04期

关键词：

D O I：

10.1039/p19900001079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The glycosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl fluoride in the presence of BF3OEt2 to give, predominantly, α-anomers has been studied. In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved. The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.

引用

页码：1079 / 1082

页数：4

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