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

被引：12

作者：

ABERG, PM ^{[1
]}

BLOMBERG, L ^{[1
]}

LONN, H ^{[1
]}

NORBERG, T ^{[1
]}

机构：

[1] BIOCARB AB, DEPT ORGAN SYNTH, S-22370 LUND, SWEDEN

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1994年 / 13卷 / 02期

关键词：

D O I：

10.1080/07328309408009185

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：

Two trisaccharide spacer glycosides, p-trifluoroacetamidophenylethyl 3-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl) -2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside and p-trifluoroacetamidophenylethyl 2-O-(alpha-L-fucopyranosyl)-3-O -(alpha-D-galactopyranosyl)-beta-D-galactopyranoside, corresponding to the human blood group A and B determinants, were synthesized. A key fucosylgalactosyl disaccharide derivative was glycosylated with galactos-aminyl or galactosyl donors, respectively. Dimethyl(thiomethyl)sulfonium tetrafluoroborate was used for thioglycoside activation in all but one coupling reaction. The small scale procedure was further developed for use in a large scale (10-100 g final product) synthesis. Large scale syntheses of some crystalline thioglycoside building blocks are also described.

引用

页码：141 / 161

页数：21

共 40 条

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