Synthesis and structure of selected quaternary N-(1,4-anhydro-5-deoxy-2,3-O-isopropylidene-D,L-ribitol-5-yl)ammonium salts

Carbohydrate Research
Eugenia SkorupaAndrzej Wiśniewski

Abstract

The syntheses have been developed for quaternary N-(1,4-anhydro-5-deoxy-2,3-O-isopropylidene-D,L-ribitol-5-yl)ammonium salts derived from five aromatic amines, pyridine, 2-methylpyridine, 3-carbamoylpyridine, 4-(N,N-dimethylamino)pyridine, and quinoline, as well as two tertiary aliphatic amines, trimethylamine and triethylamine. Reactions of 1,4-anhydro-2,3-O-isopropylidene-5-O-tosyl-D,L-ribitol with tri-n-propylamine and tri-n-butylamine were unsuccessful. The products were identified on the basis of their 1H and 13C NMR spectra. The structure of N-(1,4-anhydro-5-deoxy-2,3-O-isopropylidene-D,L-ribitol-5-yl)trimethylammonium tosylate was additionally elucidated by X-ray diffractometry.

References

Jan 1, 1989·Cancer Chemotherapy and Pharmacology·E InstitórisF Gál
Jun 20, 1986·Journal of Chromatography·K Kakehi, S Honda
Jul 13, 2000·Carbohydrate Research·M KurszewskaA Wiśniewski
Aug 2, 2002·Carbohydrate Research·Maria KurszewskaAndrzej Wiśniewski

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Citations

Apr 11, 2013·Journal of Molecular Modeling·Andrzej NowackiAndrzej Wiśniewski
Sep 21, 2013·Acta Crystallographica. Section E, Structure Reports Online·Barbara DmochowskaAndrzej Wiśniewski
May 10, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Barbara DmochowskaJanusz Madaj

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