Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose
1Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
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]
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