Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-D-hexopyranoses
2010
Abstract
Fluorinated hexopyranoses are important synthetic targets because of their utilization as probes in enzymology, medicine and structure - reactivity studies. We have prepared a full series of 1,6-anhydro-2,3,4-deoxy-4-fluoro-2,3-epimino-β-D-hexopyranoses.
The key step was reaction of trans-2,3-azidosulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields.
A convenient synthesis of D-manno epimine from a readily available 3-benzylamino derivative was also developed.