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Catalytic Stereoselective Glycosidation with Glycosyl Diphenyl Phosphates: Rapid Construction of 1,2‐ cis ‐α‐Glycosidic Linkages
Author(s) -
Koshiba Miyuki,
Suzuki Noritoshi,
Arihara Ryoichi,
Tsuda Toshifumi,
Nambu Hisanori,
Nakamura Seiichi,
Hashimoto Shunichi
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800173
Subject(s) - stereoselectivity , chemistry , glycosyl , glycosidic bond , catalysis , glycoside , glycosylation , organic chemistry , stereochemistry , medicinal chemistry , enzyme , biochemistry
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 α selectivities. The synthetic utility of this glycosidation method was demonstrated by a stereoselective synthesis of the α‐galactosylceramide KRN7000, an activator of natural killer (NK) T cells through CD1d molecules.