Highly stereocontrolled synthesis of gem-difluoromethylenated azasugars: D- and L-1,4,6-trideoxy-4,4-difluoronojirimycin.
[reaction: see text]. D-1,4,6-trideoxy-4,4-difluoronojirimycin and L-1,4,6-trideoxy-4,4-difluoronojirimycin, a novel series of gem-4,4-difluoromethylenated azasugars, were synthesized from CF3CH2OH in 10 steps. A key step was the highly diastereoselective construction of the piperidine ring via reductive amination.
Wang
Ruo-Wen
RW
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Qing
Feng-Ling
FL
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D002384:Catalysis; D018360:Crystallography, X-Ray; D050112:Imino Pyranoses / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C507940:1,4,6-trideoxy-4,4-difluoronojirimycin; D050112:Imino Pyranoses; D017485:1-Deoxynojirimycin