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

✍ Scribed by Zygfryd Smiatacz; Antonina Moczulska

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 441 KB
• Volume: 128
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85332-x

✦ Synopsis

N-p-Chlorophenyl-and N-p-methoxyphenyl-D-lyxopyranosylamines have been synthesised, and also their tri-0-acetyl, N-acetyl-tri-0-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 4C1 and 'C4 isomers. The effect of steric factors on N+O acetyl migration has been ascertained. Selective benzoylation of N-acetyl-N-aryl-a-D-~yxopyranosylamines afforded partially esterified derivatives in which the reactivity of the hydroxyl groups followed the sequence HO-4 > HO-3 > HO-2.