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

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 1 H and 13 C 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.