Novel stereocontrolled α- and β-glycosidations of mannopyranosyl sulfoxides using environmentally benign heterogeneous solid acids

被引：41

作者：

Nagai, H ^{[1
]}

Kawahara, K ^{[1
]}

Matsumura, S ^{[1
]}

Toshima, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 25期

关键词：

sulfoxide glycosidation; heterogeneous solid acid; Nafion-H; sulfated zirconia; alpha- and beta-mannopyranosides;

D O I：

10.1016/S0040-4039(01)00674-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The environmentally benign and stereocontrolled glycosidations of mannopyranosyl sulfoxides and alcohols using a heterogeneous solid acid, Nafion-H or sulfated zirconia (SO4/ZrO2) as a new activator for the direct syntheses of both the alpha- and beta -mannopyranosides have been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4159 / 4162

页数：4

共 12 条

[1] Strategies in oligosaccharide synthesis [J].

Boons, GJ .

TETRAHEDRON, 1996, 52 (04) :1095-1121

[2] Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method [J].

Crich, D ;

Sun, SX .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4506-4507

[3] Direct synthesis of beta-mannopyranosides by the sulfoxide method [J].

Crich, D ;

Sun, SX .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1198-1199

[4] Direct formation of β-mannopyranosides and other hindered glycosides from thioglycosides [J].

Crich, D ;

Sun, SX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :435-436

[5] Recent developments in oligosaccharide synthesis [J].

Davis, BG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2137-2160

[6] Recent advances in the construction of β-D-mannose and β-D-mannosamine linkages [J].

Gridley, JJ ;

Osborn, HMI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10) :1471-1491

[7]

HANESSIAN S, 1977, PREPARATIVE CARBOHYD, pCH12

[8] GLYCOSYLATION OF UNREACTIVE SUBSTRATES [J].

KAHNE, D ;

WALKER, S ;

CHENG, Y ;

VANENGEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6881-6882

[9] NEW METHODS FOR THE SYNTHESIS OF GLYCOSIDES AND OLIGOSACCHARIDES - ARE THERE ALTERNATIVES TO THE KOENIGS-KNORR METHOD [J].

SCHMIDT, RR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :212-235

[10] RECENT ADVANCES IN GLYCOSYLATION REACTIONS [J].

SINAY, P .

PURE AND APPLIED CHEMISTRY, 1991, 63 (04) :519-528

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