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Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses
- 1.0343244 - ÚCHP 2011 RIV US eng J - Journal Article
Karban, Jindřich - Sýkora, Jan - Kroutil, J. - Císařová, I. - Padělková, Z. - Buděšínský, Miloš
Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses.
Journal of Organic Chemistry. Roč. 75, č. 10 (2010), s. 3443-3446. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA AV ČR IAA400720703; GA AV ČR IAA400720706
Institutional research plan: CEZ:AV0Z40720504; CEZ:AV0Z40550506
Keywords : fluorinated hexopyranoses * synthesis * experiments
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 4.002, year: 2010
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.
Permanent Link: http://hdl.handle.net/11104/0185763
Number of the records: 1