PREPARATION OF ETHER-LINKED 2-ACETAMIDO-2-DEOXY BETA-GLYCOLIPIDS VIA ZINC-CHLORIDE PROMOTED COUPLING OF AC(4)GLCNAC-CL WITH LIPID HYDROXY-GROUPS

被引：10

作者：

KUMAR, ER ^{[1
]}

BYUN, HS ^{[1
]}

WANG, SH ^{[1
]}

BITTMAN, R ^{[1
]}

机构：

[1] CUNY QUEENS COLL,DEPT CHEM & BIOCHEM,FLUSHING,NY 11367

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(00)75823-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective glycosidation of lipid hydroxy groups has been achieved using 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glycosyl chloride as the glycosyl donor in CH2Cl2. In the presence of ZnCl2 (1 equiv.) and various ''promoters'' (1 equiv.) such as Ph(3)CCl, 18-crown-6/KCl, n-Bu(4)NBr, or Me(3)SiCl, beta-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl2 in CH2Cl2.

引用

页码：505 / 508

页数：4

共 7 条

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