The conversion of 3-C-β-D-galactopyranosyl phloroacetophenone to a spiroketal derivative

被引：12

作者：

Kumazawa, T ^{[1
]}

Chiba, M ^{[1
]}

Matsuba, S ^{[1
]}

Sato, S ^{[1
]}

Onodera, J ^{[1
]}

机构：

[1] Yamagata Univ, Fac Engn, Dept Mat Sci & Engn, Yonezawa, Yamagata 9928510, Japan

来源：

CARBOHYDRATE RESEARCH | 2000年 / 328卷 / 04期

关键词：

C-glycosylic compound; 3-C-beta-D-galactopyranosylphloroacetophenone acid treatment; spiroketal derivative; tetrahydrospiro{benzofuran-2(3H); 2; '-[2H]pyran;

D O I：

10.1016/S0008-6215(00)00126-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Treatment of 3-C-beta-D-galactopyranosylphloroacetophenone in hot water with a catalytic amount of p-toluenesulfonic acid afforded a spiroketal compound as the main product. The chirality of the spiro carbon of the product was R, which is the opposite of the spiroketal obtained by the conversion of 3-C-beta-D-glucopyranosyl phloroacetophenone under identical conditions. The structure was determined by H-1-H-1 COSY,H-1-C-13 COSY, NOESY and HMBC spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：599 / 603

页数：5

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