Synthesis of branched-chain sugars: A stereoselective route to sibirosamine, kansosamine, and vinelose from a common precursor

Abstract

Methyl 4,6-dideoxy-3- C-methyl-4-( N-methyl- N-phenylsulfonylamino)-α- l-mannopyranoside and methyl 4-amino-4,6-dideoxy-3- C-methyl-α- l-mannopyranoside, derivatives of the branched-chain amino sugars sibirosamine and kansosamine, respectively, were synthesized by nucleophilic ring-opening of methyl 3,4-anhydro-6-deoxy-3- C-methyl-α- l-talopyranoside. Catalytic reduction of methyl 6-deoxy-2,3- O-isopropylidene-3- C-methyl-α- l- lyxo-hexopyranosid-4-ulose gave the axial alcohol methyl 6-deoxy-2,3- O-isopropylidene-3- C-methyl-α- l-talopyranoside, a known precursor to vinelose.