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A short and efficient synthesis of a-(1>3)-C-linked disaccharides containing 2 deoxyhexopyranoses

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F04%3A00012727" target="_blank" >RIV/60461373:22330/04:00012727 - isvavai.cz</a>

  • Result on the web

  • DOI - Digital Object Identifier

Alternative languages

  • Result language

    angličtina

  • Original language name

    A short and efficient synthesis of a-(1>3)-C-linked disaccharides containing 2 deoxyhexopyranoses

  • Original language description

    Protected a-D-glucopyranosylacetaldehyde was converted by Wittig reaction with (thiazol 2 yl)carbonylmethylenetriphenyl phosphorane into the corresponding substituted 1-oxa-1,3-butadiene which by hetero-Diels-Alder reaction with ethyl vinyl ether afforded a mixture of two diastereoisomeric dihydropyran derivatives. These were separated by chromatography and the thiazol ring was transformed into an aldehyde group. Subsequent hydroboration afforded a-C-(1>3)-linked disaccharides containing 2-deoxyhexopyranoses of D- or L- configuration.

  • Czech name

    Krátká a efektivní syntéza a-(1>3)-C-disacharidů obsahujících 2 deoxyhexopyranosu

  • Czech description

    Chráněný ?-D-glukopyranosylacetaldehyd byl pomocí Wittigovy reakce s (thiazol 2 yl)karbonylmethylenetrifenylfosforanem převeden na odpovídající 1-oxa-1,3-butadien, který reakcí s ethylvinyletherem poskytl směs dvou diastereoisomerních derivátu dihydropyranu. Tato byla chromatograficky rozdělena a thiazolový kruh byl transformován na aldehyd. Následná hydroborace poskytla ?-C-(1#3)-disacharidy obsahující 2-deoxyhexopyranosu s D-, nebo s L- konfiguraci.

Classification

  • Type

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

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)

Others

  • Publication year

    2004

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Tetrahedron: Asymmetry

  • ISSN

    0957-4166

  • e-ISSN

  • Volume of the periodical

    15

  • Issue of the periodical within the volume

    6

  • Country of publishing house

    BE - BELGIUM

  • Number of pages

    8

  • Pages from-to

    1033-1041

  • UT code for WoS article

  • EID of the result in the Scopus database