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

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F10%3A00343244" target="_blank" >RIV/61388963:_____/10:00343244 - isvavai.cz</a>

  • Alternative codes found

    RIV/67985858:_____/10:00343244

  • Result on the web

    —

  • DOI - Digital Object Identifier

    —

Alternative languages

  • Result language

    angličtina

  • Original language name

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

  • Original language description

    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-?-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.

  • Czech name

    —

  • Czech description

    —

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CF - Physical chemistry and theoretical chemistry

  • OECD FORD branch

    —

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Others

  • Publication year

    2010

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Organic Chemistry

  • ISSN

    0022-3263

  • e-ISSN

    —

  • Volume of the periodical

    75

  • Issue of the periodical within the volume

    10

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    4

  • Pages from-to

    —

  • UT code for WoS article

    000277531200033

  • EID of the result in the Scopus database

    —

Similar results(10)

Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-Elinin-4-fluoro-beta-D-hexopyranosesSynthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-D-hexopyranosesSynthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.