New class of quaternary ammonium salts, derivatives of methyl d-glucopyranosides

The synthesis and structures of selected quaternary N-(methyl 2,3,4-tri- O-acetyl-6-deoxy-α- and -β- d-glucopyranoside-6-yl)ammonium salts are described. Reactions of two aromatic and two aliphatic amines with methyl 6- O- p-toluenesulfonyl-α- d-glucopyranoside or methyl 6- O- p-toluenesulfonyl-β- d-glucopyranoside were performed on a micro-scale. The synthesis and preparative isolation methods have been developed for quaternary N-(methyl 2,3,4-tri- O-acetyl-6-deoxy-α- and -β- d-glucopyranoside-6-yl)ammonium salts derived from three amines: trimethylamine, 2-methylpyridine, and pyridine. The reaction products were examined with 1H, 13C NMR spectroscopy. N-(Methyl 2,3,4-tri- O-acetyl-6-deoxy-β- d-glucopyranoside-6-yl)trimethylammonium tosylate was additionally analyzed with X-ray crystallography.