Synthèse du méthyl-2-acétamido-2-désoxy-β- D-glucofuranoside et de dérivés

Abstract

Methyl 2-acetamido-2-deoxy-5,6- O-isopropylidene-β- D-glucofuranoside was prepared in excellent yield from methyl 2-benzamido-2-deoxy-5,6- O-isopropylidene-β- D-glucofuranoside by alkaline hydrolysis, followed by selective N-acetylation. Treatment with 60% acetic acid at room temperature gave syrupy methyl 2-acetamido-2-deoxy-β- D-glucofuranoside, characterized by a crystalline tri- O-p-nitrobenzoyl derivative. The same treatment, at 100° gave methyl 2-acetamido-2-deoxy-β- D-glucopyranoside. In an alternative procedure, the selective N-acetylation was performed after acetic acid hydrolysis of methyl 2-amino-2-deoxy-5,6- O-isopropylidene-β- D-glucofuranoside. Several derivatives of methyl 2-acetamido-2-deoxy-β- D-glucofuranoside were prepared and compared with the corresponding pyranosides. The furanoside structure was clearly demonstrated by mass spectrometry and periodate oxidation.