title: Synthesis of all configurational isomers of 1,6-anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-d-hexopyranoses.
abstract: We have prepared a full series of 1,6-anhydro-2,3,4-trideoxy-4-fluoro-2,3-epimino-beta-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.
authors.affiliation: Institute of the Chemical Process Fundamentals of the ASCR, Praha, Czech Republic. karban@icpf.cas.cz
authors.forename: Jindrich
authors.initials: J
authors.lastname: Karban
authors.forename: Jan
authors.initials: J
authors.lastname: Sýkora
authors.forename: Jirí
authors.initials: J
authors.lastname: Kroutil
authors.forename: Ivana
authors.initials: I
authors.lastname: Císarová
authors.forename: Zdenka
authors.initials: Z
authors.lastname: Padelková
authors.forename: Milos
authors.initials: M
authors.lastname: Budesínský
mesh_terms: D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001386:Azides; D002241:Carbohydrates