Solid-phase synthesis of complex oligosaccharides using azidoglucose as a glycosyl acceptor

Article abstract of DOI:10.1002/ejoc.200400111

The solid phase synthesis of oligosaccharides 1-3 was performed on Merrifield resin. These syntheses are based on the hydroxymethylbenzyl benzoate spacer-linker system and, for regioselective chain extension, the use of O-glycosyl trichloroacetimidates as glycosyl donors containing temporary O-Fmoc protection. The important lactosamine-containing oligosaccharides 1-3 are accessible in excellent yields by using a 2-azidoglucose residue as the glucosamine building block adjacent to the spacer-linker system. Only standard amounts of the glycosyl donor are employed in this solid phase oligosaccharide synthesis and we did not have to resort to any capping procedures. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.