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Stereoselective preparation of four 3-C-mannosylated D- and L-glucals from a single starting compound

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F11%3A43892055" target="_blank" >RIV/60461373:22330/11:43892055 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1016/j.tet.2011.04.044" target="_blank" >http://dx.doi.org/10.1016/j.tet.2011.04.044</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.tet.2011.04.044" target="_blank" >10.1016/j.tet.2011.04.044</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Stereoselective preparation of four 3-C-mannosylated D- and L-glucals from a single starting compound

  • Original language description

    The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -} 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  • Czech name

  • Czech description

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

    <a href="/en/project/GA203%2F08%2F1124" target="_blank" >GA203/08/1124: Stereoselective synthesis of disaccharide mimics as non-hydrolysable epitopes of vital glycoconjugates</a><br>

  • 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

    2011

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Tetrahedron

  • ISSN

    0040-4020

  • e-ISSN

  • Volume of the periodical

    67

  • Issue of the periodical within the volume

    27

  • Country of publishing house

    IE - IRELAND

  • Number of pages

    13

  • Pages from-to

    4967-4979

  • UT code for WoS article

    000292721000003

  • EID of the result in the Scopus database