SYNTHESIS OF DOUBLE-CHAIN BIS-SULFONE NEOGLYCOLIPIDS OF THE 2'-DEOXYGLOBOTRIOSE, 3'-DEOXYGLOBOTRIOSE, AND 6'-DEOXYGLOBOTRIOSE

被引：22

作者：

ZHANG, ZY

MAGNUSSON, G

机构：

[1] LUND UNIV,CTR CHEM,S-22100 LUND,SWEDEN

[2] LUND UNIV,LUND INST TECHNOL,S-22100 LUND,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 22期

关键词：

D O I：

10.1021/jo00127a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Partially protected 2-(trimethylsilyl)ethyl deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2'-, 3'-, and 6'-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

引用

页码：7304 / 7315

页数：12

共 40 条

[11]

HAATAJA S, 1993, J BIOL CHEM, V268, P4311

[12]

HAATAJA S, 1994, J BIOL CHEM, V269, P27466

[13] PATHOGENESIS OF SHIGELLA DIARRHEA .11. ISOLATION OF A SHIGELLA TOXIN-BINDING GLYCOLIPID FROM RABBIT JEJUNUM AND HELA-CELLS AND ITS IDENTIFICATION AS GLOBOTRIAOSYLCERAMIDE [J].