Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses.
[reaction: see text] The enantioselective syntheses of C-6 O-TBS- and N-Cbz-protected 2-deoxy- and 2,3-dideoxysugars have been achieved in 6-8 steps from furfural. A combination of chemo-, regio-, and diastereoselective oxidation and reduction reactions produced deoxysugars with various C-6 substitution. A key development of this route was the use of o-nitrobenzenesulfonylhydrazide (NBSH) as a diimide precursor. These overall procedures allow for the synthesis of eight deoxysugars in either enantiomeric form.
Haukaas
Michael H
MH
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
O'Doherty
George A
GA
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D006601:Hexoses / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C458161:2,3-dideoxyhexose; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D006601:Hexoses; D007202:Indicators and Reagents; D009005:Monosaccharides