Synthesis of 4-nitrophenyl O-(2-acetamido-2-deoxy-β- d-glucopyranosyl)-(1 → 2)- O-(6- O-methyl-α- d-mannopyranosyl)-(1 → 6)-β- d-glucopyranoside and its 4′,6′-di- O-methyl analog. Potential inhibitors of N-acetylglucosaminyl-transferase V (GnT-V)

Abstract

O-(2-Acetamido-3,4,6-tri- O-acetyl-2-deoxy-β- d-glucopyranosyl)-(1 → 2)-3,4,-di- O-acetyl-6- O-methyl-α- d-mannopyranosyl bromide and O-(2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β- d-glucopyranosyl)-(1 → 2)-3- O-acetyl-4,6-di- O-methyl-α- d-mannopyranosyl bromide were each condensed with 4-nitrophenyl 2,3-di- O-acetyl-β- d-glucopyranoside, and the products were deprotected to yield, respectively, β- d-Glc pNAc-(1 → 2)-6- O-Me-α- d-Man p-(1 → 6)-β- d-Glc p and β- d-Glc pNAc-(1 → 2)-4,6-di- O-Me-α- d-Man p-(1 → 6)-β- d-Glc p, as their 4-nitrophenyl glycosides. These trisaccharides are expected to function as inhibitors for N-acetylglucosaminyltransferase V.