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An Amination-Cyclization Cascade Reaction for Iminosugar Synthesis Using Minimal Protecting Groups.

Alex A Hunt-PainterBenjamin M DeebleBridget L StockerMattie S M Timmer
Published in: ACS omega (2022)
The development of a one-step amination-cyclization cascade reaction for the synthesis of N-substituted iminosugars from iodo-pentoses and hexoses is reported. This novel methodology allows for the stereoselective conversion of easily accessible iodo-aldoses and iodo-ketoses into iminosugars in a single step, in highly efficient yields (63-95%), and in aqueous media. Furthermore, the use of functionalized amines allows for the synthesis of N-functionalized iminosugars without additional steps. To illustrate this methodology, a number of biologically important iminosugars were prepared, including 1-deoxynojirimycin, (3 S ,4 R ,5 S ,6 R )-azepane-3,4,5,6-tetraol, and N-functionalized 1-deoxymannojirimycins.
Keyphrases
  • highly efficient
  • quantum dots
  • molecularly imprinted
  • ionic liquid
  • high resolution
  • electron transfer
  • tandem mass spectrometry