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

Authors
KUMAR ER BYUN HS WANG SH BITTMAN R
Citation
Er. Kumar et al., PREPARATION OF ETHER-LINKED 2-ACETAMIDO-2-DEOXY BETA-GLYCOLIPIDS VIA ZINC-CHLORIDE PROMOTED COUPLING OF AC(4)GLCNAC-CL WITH LIPID HYDROXY-GROUPS, Tetrahedron letters, 35(4), 1994, pp. 505-508
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
4
Year of publication
1994
Pages
505 - 508
Database
ISI
SICI code
0040-4039(1994)35:4<505:POE2BV>2.0.ZU;2-T
Abstract
Stereoselective glycosidation of lipid hydroxy groups has been achieve d using tamido-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 i nitial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl2 in CH2Cl2.