Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD

被引：42

作者：

Chayajarus, K ^{[1
]}

Chambers, DJ ^{[1
]}

Chughtai, MJ ^{[1
]}

Fairbanks, AJ ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol048427o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(GRAPHICS) Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.

引用

页码：3797 / 3800

页数：4

共 31 条

[1]

Aloui M, 2002, CHEM-EUR J, V8, P2608, DOI 10.1002/1521-3765(20020603)8:11<2608::AID-CHEM2608>3.0.CO

[2]

2-4

[3] SYNTHESIS OF 1,2-CIS-LINKED GLYCOSIDES USING DIMETHYL(METHYLTHIO)SULFONIUM TRIFLATE AS PROMOTER AND THIOGLYCOSIDES AS GLYCOSYL DONORS [J].