American Chemical Society
jo1000912_si_007.cif (17.42 kB)

Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-d-hexopyranoses

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posted on 2010-05-21, 00:00 authored by Jindřich Karban, Jan Sýkora, Jiří Kroutil, Ivana Císařová, Zdeňka Padělková, Miloš Buděšínský
We have prepared a full series of 1,6-anhydro-2,3,4-trideoxy-4-fluoro-2,3-epimino-β-d-hexopyranoses. The key step was the reaction of azido sulfonates 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-mannoepimine from a readily available 3-benzylamino derivative was also developed.