Solid‐Phase Synthesis of Complex Oligosaccharides Using Azidoglucose as a Glycosyl Acceptor

Abstract

AbstractThe 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)