Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose

Org Lett. 2001 Nov 29;3(24):3899-902. doi: 10.1021/ol016743m.

Abstract

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]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Sugars / chemical synthesis*
  • Glucosamine / analogs & derivatives*
  • Glucosamine / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Rhamnose / analogs & derivatives
  • Rhamnose / chemical synthesis*
  • Stereoisomerism

Substances

  • 6-amino-6-deoxymannose
  • 6-amino-6-deoxytalose
  • Amino Sugars
  • 6-amino-6-deoxyglucopyranose
  • Glucosamine
  • Rhamnose