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

Carbohydr Res. 1988 Dec 1;183(2):277-85. doi: 10.1016/0008-6215(88)84080-1.

Abstract

Methyl 4,6-dideoxy-3-C-methyl-4-(N-methyl-N-phenylsulfonylamino)-alpha-L- mannopyranoside and methyl 4-amino-4,6-dideoxy-3-C-methyl-alpha-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-alpha-L-talopyranoside. Catalytic reduction of methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-alpha-L-lyxo-hexopyrano sid-4-ulose gave the axial alcohol methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-alpha-L-talopyranoside, a known precursor to vinelose.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Azotobacter
  • Carbohydrate Conformation
  • Carbohydrates / chemical synthesis*
  • Chemical Phenomena
  • Chemistry
  • Glucosamine / chemical synthesis
  • Hexosamines / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Methylglycosides / chemical synthesis*

Substances

  • Carbohydrates
  • Hexosamines
  • Methylglycosides
  • vinelose
  • sibirosamine
  • kanosamine
  • Glucosamine