1226996-74-2Relevant articles and documents
Synthesis of all configurational isomers of 1,6-anhydro-2,3,4-trideoxy-2,3- epimino-4-fluoro-β- d -hexopyranoses
Karban, Jindrich,Sykora, Jan,Kroutil, Jiri,Cisarova, Ivana,Padelkova, Zdenka,Budesinsky, Milos
supporting information; experimental part, p. 3443 - 3446 (2010/07/05)
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 LiAlH 4 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.