An economical synthesis of Lewis X, sialyl Lewis X and their alpha-galactosyl analogues

被引：15

作者：

Dekany, G ^{[1
]}

Wright, K ^{[1
]}

Toth, I ^{[1
]}

机构：

[1] UNIV LONDON,SCH PHARM,LONDON WC1N 1AX,ENGLAND

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1997年 / 16卷 / 07期

关键词：

D O I：

10.1080/07328309708005732

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：

Economical syntheses of the Lewis X trisaccharide 8 and sialyl Lewis X tetrasaccharide 18 epitopes and the syntheses of the alpha-galactosyl epimers 9 and 20 of these structures are described. Thioglycosides 2, 5, 11 and 15 were used as glycosyl donors to construct the desired compounds in a stepwise manner in dimethyl(methylthio)sulphonium triflate promoted couplings. Benzyl 3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-acetamido-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside (4) was a key structure in these syntheses, and was synthesised in multi-gram scale.

引用

页码：983 / 999

页数：17

共 20 条

[1] LARGE-SCALE SYNTHESIS OF 2 TRISACCHARIDE SPACER GLYCOSIDES CORRESPONDING TO THE BLOOD-GROUP A AND B DETERMINANTS USING THIOGLYCOSIDES AND DIMETHYL(THIOMETHYL)SULFONIUM TETRAFLUOROBORATE (DMTSB) AS PROMOTER [J].