1.
Chem Asian J
; 3(8-9): 1664-77, 2008 Sep 01.
Artigo
em Inglês
| MEDLINE
| ID: mdl-18604830
RESUMO
A commercially available 0.1 M solution of HClO(4) in dioxane has been shown to catalyze the glycosidation of glycosyl diphenyl phosphates. The per-O-benzyl-protected glucosyl and galactosyl donors and the 3,4,6-tri-O-acetyl-2-azido-2-deoxygalactosyl donor each react with a range of acceptor alcohols in the presence of 0.05-0.2 equiv of HClO(4) in dioxane/Et(2)O (1:1) to afford glycosides in good yields with good to excellent alpha selectivities. The synthetic utility of this glycosidation method was demonstrated by a stereoselective synthesis of the alpha-galactosylceramide KRN7000, an activator of natural killer (NK) T cells through CD1d molecules.