N-aryl- d-lyxopyranosylamines, their acyl derivatives, and selective benzoylation of N-acetyl- N-aryl-α- d-lyxopyranosylamines

Abstract

N- p-Chlorophenyl- and N- p-methoxyphenyl- d-lyxopyranosylamines have been synthesised, and also their tri- O-acetyl, N-acetyl-tri- O-acetyl, and N-acetyl derivatives. The configurations and conformations of these compounds have been established. Some derivatives of the N-aryl- d-lyxopyranosylamines were obtained as two stable, crystalline 4 C 1 and 1 C 4 isomers. The effect of steric factors on N→ O acetyl migration has been ascertained. Selective benzoylation of N-acetyl- N-aryl-α- d-lyxopyranosylamines afforded partially esterified derivatives in which the reactivity of the hydroxyl groups followed the sequence HO-4 > HO-3 > HO-2.