Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose.
The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars. [reaction: see text]
Haukaas
M H
MH
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
O'Doherty
G A
GA
D000606:Amino Sugars / Q000138:chemical synthesis*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D012210:Rhamnose / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism
C442890:6-amino-6-deoxymannose; C442891:6-amino-6-deoxytalose; D000606:Amino Sugars; C075821:6-amino-6-deoxyglucopyranose; D005944:Glucosamine; D012210:Rhamnose