A versatile strategy for the synthesis of complex type N-glycans: Synthesis of diantennary and bisected diantennary oligosaccharides1

Article abstract of DOI:10.1016/S0040-4039(98)00246-9

Based on readily available glucose, 2-azido-glucose, mannose, and N- phthaloyllactosamine building blocks 5, 6, 8, and 13 a highly versatile strategy for the synthesis of complex type and bisected complex type N- glycan residues is established; this is demonstrated for the synthesis of nonasaccharide 1 and decasaccharide 2, respectively. The glucose residue g finally provides regioselective access to the 3-, 4-, and/or 6-hydroxy groups for antenna attachment, introduction of the bisecting N-acetylglucosamine residue, and epimerisation at C-2 in order to generate the required β- linked mannosyl residue c.