Synthesis of three oligosaccharides that form part of the complex type of carbohydrate moeity of glycoproteins containing intersecting N-acetylglucosamine

Abstract

The oligosaccharides (1)–(3) have been synthesized by conventional methods. 4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-(α-D-mannopyranosyl)-D-mannose (1), 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-bis-O-[2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-D-mannose (2), and 3,6-bis-O-{2-O-[2-acetamido-2-deoxy-4-O-(β-D-galacto-pyranosyl)-β-D-glucopyranosyl]-α-D-mannopyranosyl}-4-O-(2-acetamido-2-deoxy-β-D-glucopy-ranosyl)-D-mannose (3) represent partial structures of the carbohydrate moiety in those glycoproteins of the complex type in which a 2-acetamido-2-deoxy-β-D-glucopyranosyl group is linked to O-4 of the β-D-mannopyranosyl residue of the invariant core (4). p-Methoxybenzyl groups were used for temporary protection of hydroxy groups