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EN
ČeštinaEnglish

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43923761" target="_blank" >RIV/60461373:22310/21:43923761 - isvavai.cz</a>

  • Result on the web

    <a href="https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-85.pdf" target="_blank" >https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-85.pdf</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.3762/bjoc.17.85" target="_blank" >10.3762/bjoc.17.85</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

  • Original language description

    Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N-acetyl-D-glucosamine and D-galactosamine analogs. The key intermediates are the corresponding multiply fluorinated glucosazide and galactosazide thioglycosides prepared from deoxyfluorinated 1,6-anhydro-2-azido-beta-D-hexopyranose precursors by ring-opening reaction with phenyl trimethylsilyl sulfide. Nucleophilic deoxyfluorination at C4 and C6 by reaction with DAST, thioglycoside hydrolysis and azide/acetamide transformation completed the synthesis.

  • Czech name

    —

  • Czech description

    —

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

    —

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    —

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2021

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Beilstein Journal of Organic Chemistry

  • ISSN

    1860-5397

  • e-ISSN

    —

  • Volume of the periodical

    17

  • Issue of the periodical within the volume

    11.3.2021

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    10

  • Pages from-to

    1086-1095

  • UT code for WoS article

    000651417700001

  • EID of the result in the Scopus database

    2-s2.0-85106378865

Similar results(10)

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide thiodonors.The Effect of Deoxyfluorination and O-Acylation on the Cytotoxicity of N-Acetyl-D-Gluco- and D-Galactosamine Hemiacetals.Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.