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  • Title: New class of quaternary ammonium salts, derivatives of methyl D-glucopyranosides.
    Author: Pellowska-Januszek L, Dmochowska B, Skorupa E, Chojnacki J, Wojnowski W, Wiśniewski A.
    Journal: Carbohydr Res; 2004 Jun 01; 339(8):1537-44. PubMed ID: 15178398.
    Abstract:
    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.
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