New class of quaternary ammonium salts, derivatives of methyl D-glucopyranosides.
Reactions of two aromatic and two aliphatic amines with methyl 6-O-p-toluenesulfonyl-alpha-D-glucopyranoside or methyl 6-O-p-toluenesulfonyl-beta-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-alpha- and -beta-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-beta-d-glucopyranoside-6-yl)trimethylammonium tosylate was additionally analyzed with X-ray crystallography.
Pellowska-Januszek
Lucyna
L
Department of Chemistry, University of Gdańsk, 18 Sobieskiego, PL-80-952 Gdańsk, Poland.
Dmochowska
Barbara
B
Skorupa
Eugenia
E
Chojnacki
Jarosław
J
Wojnowski
Wiesław
W
Wiśniewski
Andrzej
A
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008757:Methylglucosides / Q000737:chemistry*; D008958:Models, Molecular; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification*
D008757:Methylglucosides; D000644:Quaternary Ammonium Compounds; C027020:methylglucoside