An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-beta-D-glucosylglycerol ethers by epoxidation of an allyl beta-D-glucopyranoside asymmetrically induced by the glucide moiety

被引：19

作者：

Bellucci, G ^{[1
]}

Catelani, G ^{[1
]}

Chiappe, C ^{[1
]}

DAndrea, F ^{[1
]}

Grigo, G ^{[1
]}

机构：

[1] DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(97)00041-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1-O-Hexadecyl and 1,2-di-O-hexadecyl-3-O-(beta-D-glucopyranosyl)-sn-glycerol ethers were obtained by regiospecific opening of the oxirane ring of the 2',3'-epoxypropyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranoside synthetized by stereoselective epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside asymmetrically induced by the glucide moiety. (C) 1997 Published by Elsevier Science Ltd.

引用

收藏

页码：765 / 773

页数：9

相关论文

共 18 条

[1] DIASTEREOSELECTIVE BROMINATION OF ALLYL GLYCOSIDES USING TETRABUTYLAMMONIUM TRIBROMIDE [J].

BELLUCCI, G ;

CHIAPPE, C ;

DANDREA, F .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :221-230

[2] A SIMPLE AND HIGHLY DIASTEREOSELECTIVE PREPARATION OF GLYCAL EPOXIDES USING THE MCPBA-KF COMPLEX [J].

BELLUCCI, G ;

CATELANI, G ;

CHIAPPE, C ;

DANDREA, F .

TETRAHEDRON LETTERS, 1994, 35 (45) :8433-8436

[3]

BJORKLING F, 1988, TETRAHEDRON, V44, P2957

[4] CARBOHYDRATES AS CHIRAL AUXILIARIES - THE ASYMMETRIC EPOXIDATION REACTION OF OLEFINS [J].

CHARETTE, AB ;

COTE, B .

TETRAHEDRON-ASYMMETRY, 1993, 4 (11) :2283-2286

[5] CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS [J].

CHARETTE, AB ;

COTE, B ;

MARCOUX, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8166-8167

[6]

COLOMBO D, 1995, TETRAHEDRON LETT, V36, P4865

[7] THE PHYSICAL-PROPERTIES OF GLYCOLIPIDS [J].

CURATOLO, W .

BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 906 (02) :111-136

[8] STEREOSELECTIVE GLYCOSIDIC COUPLING REACTIONS OF FULLY BENZYLATED 1,2-ANHYDRO SUGARS WITH N-TOSYL-L-SERINE METHYL-ESTER OR N-BENZYLOXYCARBONYL-L-SERINE METHYL-ESTER [J].

DU, YG ;

KONG, FZ .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (03) :341-352

[9]

GODDAT J, 1994, CARBOHYD RES, V252, P159

[10] ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].

HALCOMB, RL ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666