PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE-TRANSFER-CATALYZED BENZOYLATION AND BENZYLATION

被引：96

作者：

GAREGG, PJ ^{[1
]}

KVARNSTROM, I ^{[1
]}

NIKLASSON, A ^{[1
]}

NIKLASSON, G ^{[1
]}

SVENSSON, SCT ^{[1
]}

机构：

[1] LINKOPING UNIV,DEPT CHEM,S-58183 LINKOPING,SWEDEN

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1993年 / 12卷 / 07期

关键词：

D O I：

10.1080/07328309308020107

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：

Partial substitution by phase transfer catalysis giving monobenzoylated and monobenzylated products from 2,3- and from 4,6-diols in ethyl 1-thio-D-hexopyranosides with the beta-gluco-, beta-galacto- and alpha-manno-configurations are described. Two disaccharide thioglucoside diols with either the 2',3'-hydroxyl groups or the 4',6'-hydroxyl groups free were included in the study. Good yields of monosubstitution products are obtained after chromatographic separations, making this a useful method for obtaining protected thioglycosides with a single hydroxyl group for further manipulations.

引用

页码：933 / 953

页数：21

共 23 条

[1] GLYCOSYLATION WITH THIOGLYCOSIDES ACTIVATED BY DIMETHYL(METHYLTHIO)SULFONIUM TETRAFLUOROBORATE - SYNTHESIS OF 2 TRISACCHARIDE GLYCOSIDES CORRESPONDING TO THE BLOOD GROUP-A AND GROUP-B DETERMINANTS [J].