Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst

被引：23

作者：

Jyojima, T ^{[1
]}

Miyamoto, N ^{[1
]}

Ogawa, Y ^{[1
]}

Matsumura, S ^{[1
]}

Toshima, K ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

glycosidation; olivose; olivoside; montmorillonite K-10; environmentally benign synthesis;

D O I：

10.1016/S0040-4039(99)00924-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel stereocontrolled glycosidations of 3,4-di-O-protected olivoses and alcohols using a heterogeneous and environmentally benign solid acid, montmorillonite K-10, have been developed. The glycosidations of the 3-O-Ac-4-O-TBS-olivose (4) and various alcohols using montmorillonite K-10 in CH2Cl2 at 25 degrees C exclusively gave the corresponding alpha-olivosides in high yields. On the other hand, the corresponding beta-olivosides were predominately obtained by the glycosidations of the 3-O-TBS-4-O-Ac-olivose (5) and various alcohols under similar conditions. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：5023 / 5026

页数：4

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