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
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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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
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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
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