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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
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SYSNO ASEP 0343244 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Author(s) Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Sýkora, Jan (UCHP-M) RID, ORCID, SAI
Kroutil, J. (CZ)
Císařová, I. (CZ)
Padělková, Z. (CZ)
Buděšínský, Miloš (UOCHB-X) RID, ORCIDSource Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 75, č. 10 (2010), s. 3443-3446Number of pages 4 s. Language eng - English Country US - United States Keywords fluorinated hexopyranoses ; synthesis ; experiments Subject RIV CF - Physical ; Theoretical Chemistry R&D Projects IAA400720703 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) IAA400720706 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40720504 - UCHP-M (2005-2011) AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000277531200033 DOI 10.1021/jo1000912 Annotation 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. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2011
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