Synthesis of branched-chain sugars: a stereoselective route to sibirosamine, kansosamine, and vinelose from a common precursor.
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.
Giuliano
R M
RM
Department of Chemistry, Villanova University, PA 19085.
Kasperowicz
S
S
D001395:Azotobacter; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000138:chemical synthesis; D006595:Hexosamines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000138:chemical synthesis*
D002241:Carbohydrates; D006595:Hexosamines; D008759:Methylglycosides; C058355:vinelose; C058354:sibirosamine; C014968:kanosamine; D005944:Glucosamine