Synthesis of epimeric 2-acetamido-2-deoxyheptoses from D-mannose, D-galactose, and D-talose

Abstract

D-Mannose, D-galactose, and D-talose were converted via the action of nitromethane to their corresponding 3,4,5,6,7-pentaacetoxy-1-nitro-1-heptene derivatives which on treatment with ammonia afforded theepimeric2-acetamido-1,2-dideoxy-1-nitroheptitol derivatives. The 2-acetamido-1,2-dideoxy-1-nitroheptitols were converted via the Nef reaction to the corresponding 2-acetamido-2-deoxyheptoses. The configuration of the 2-acetamido-2-deoxyheptoses was established by their degradation to known 2-acetamido-2-deoxyhexitol derivatives. The properties of the 2-acetamido-2-deoxyheptoses are described.