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

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.