Synthesis of Di- and Tri-saccharides Having the Sequences [β-D-GlcNAc]_n (1 → X)-α-d-Man in the Glycan of glycopeptides

Abstract

Five model di- and tri-saccharides corresponding to the part structures of the glycan of glycopeptides were synthesized with regio- and stereo-control. They were as follows: methyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside, methyl 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside, methyl 6-O-(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)-α-D-mannopyranoside, methyl 3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside, and methyl 2,4-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside. Some aspects of ¹H- and ¹³C-NMR data of these synthetic saccharides were also described.