Synthesis of p-nitrophenyl 2-acetamido-2-deoxy-O-β-Dgalactopyranosyl-β-D-glucopyranosides

Reaction of p-nitrophenyl 2-acetamido-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside (2) with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (3) under the usual conditions, followed by removal of the p-methoxybenzylidene group and O-deacylation, produced crystalline p-nitrophenyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranoside (6). Starting from p-nitrophenyl 2-acetamido 3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside, the synthesis of p-nitrophenyl 2-acetamido-2-deoxy-6-O-β-D-galactopyranosyl-β-D-glucopyranoside was also accomplished.