2010 Volume 58 Issue 1 Pages 1-12
A regio- and stereo-selective parallel synthesis of oligosaccharides on a solid support was successfully achieved by a combination of a novel α-selective glycosidation procedure and a uni-chemo hydroxyl protection (UCHP) procedure. The α-selective glycosidation of dibutyl 3,4-di-O-benzoyl-2,6-di-O-benzyl-α/β-D-galactopyranosyl phosphate in cyclopentyl methyl ether (as an ethereal solvent for effective swelling of the polystyrene resin) proceeded smoothly and in relatively high yield. Five types of trigalactoses [Galα1-3Galβ1-3Gal, Galβ1-3(Galα1-4)Gal, Galα1-4Galβ1-3Gal, Galα1-3Galβ1-4Gal, and Galα1-4Galβ1-4Gal] were successfully synthesized on a solid support as a model of a combinatorial oligosaccharide library.