STEREOSELECTIVE PHASE-TRANSFER-CATALYZED SYNTHESES OF GLYCOSYLOXYSUCCINIMIDES AND THEIR TRANSFORMATIONS INTO GLYCOPROBES

被引：57

作者：

CAO, SD ^{[1
]}

TROPPER, FD ^{[1
]}

ROY, R ^{[1
]}

机构：

[1] UNIV OTTAWA,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

TETRAHEDRON | 1995年 / 51卷 / 24期

关键词：

D O I：

10.1016/0040-4020(95)00325-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosyloxysuccinimides of D-galactose, D-glucose, N-acetyl-D-glucosamine, Lactose, maltose (7-11) and sialic acid (13) were prepared from their glycosyl halides under PTC conditions. Ring opening of the succinimide moieties occurred with sodium hydroxide or methoxide to provide extended aglycons, while treatment of 8 with hydrazine afforded O-galactopyranosylhydroxylamine 17. Treatment of 9 with tris(2-aminoethyl)amine gave divalent cluster 20 which upon further treatment with fluorescein isothiocyanate provided divalent glycoprobe 21.

引用

页码：6679 / 6686

页数：8

共 22 条

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