Reaction of amines with the bisulphite addition compound of 5-Amino-5-deoxy-D-xylose: Conversion to piperidine derivatives

Abstract

The bisulphite addition compound (1) of 5-amino-5-deoxy-D-xylose reacted with cyclohexylamine to form the acyclic derivative (11). With ammonia, benzylamine, morpholine, and piperidine, corresponding salts (IV) of the piperidine derivative D-ido(gluco)-3,4,5-trihydroxy-2-sulphopiperidine (VIII), were isolated. Removal of the amine yielded the crystalline bisulphite addition compound (VIII). Acetylation in the presence of pyridine of the different amine salts (11, IV) and of (VIII) gave an identical acetate (VII), l-acetyl-D-ido(gluco)-3,4,5-triacetoxy-2-sulphopiperidine, isolated as the pyridine salt. Deacetylation of (VII) with barium methoxide gave the barium salt (IX). Oxidation of (IX) with sodium periodate liberated one mole of formic acid, confirming the presence of a six-membered ring containing nitrogen. The significance of these results in the inhibition of non-enzymic browning by sulphur dioxide is discussed.