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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GA203%2F08%2F1124" target="_blank" >GA203/08/1124: Stereoselektivní syntéza disacharidových analogů jako nehydrolyzovatelných epitopů v důležitých glykokonjugátech</a><br>

Návaznosti

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

Rok uplatnění

2011

Kód důvěrnosti údajů

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

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Svazek periodika

67

Číslo periodika v rámci svazku

27

Stát vydavatele periodika

IE - Irsko

Počet stran výsledku

13

Strana od-do

4967-4979

Kód UT WoS článku

000292721000003

EID výsledku v databázi Scopus

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