Microwave-assisted synthesis of D-glucuronic acid derivatives using cost-effective solid acid catalysts

[en] Monomode microwave-assisted coupling of D-glucuronic acid with alcohols, in the presence of various impregnated acid catalysts, was successfully performed, affording in almost quantitative yields the corresponding monosubstituted b-D-glucofuranosidurono-6,3-lactones in less than 10 min at 85°C. This study evidences the synergy of microwaves and impregnated acid catalysts as a fast and clean strategy in the field of carbohydrate chemistry.

Disciplines :

Chemistry

Author, co-author :

Richel, Aurore ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Laurent, Pascal ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Wathelet, Bernard ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Wathelet, Jean-Paul ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Paquot, Michel ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Language :

English

Title :

Microwave-assisted synthesis of D-glucuronic acid derivatives using cost-effective solid acid catalysts

Publication date :

2010

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Pages :

1356-1360

Peer reviewed :

Peer Reviewed verified by ORBi

Name of the research project :

Programme d'Excellence TECHNOSE

Funders :

DGTRE - Région wallonne. Direction générale des Technologies, de la Recherche et de l'Énergie

Available on ORBi :

since 27 January 2010

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General procedure for the microwave-assisted synthesis of compounds 1-7: d-GlcA (200 mg, 1.03 mmol), alcohol (5-25 equiv) and the acid catalyst were introduced together in a specific 10 mL microwave vial. The vial was next placed in the microwave cavity and irradiated under stirring. Control of the temperature during the experiment was assigned by an infrared detector. For classical thermally driven reactions, the reactions were performed under agitation in a thermostated oil bath. After heating, the crude mixture was filtrated to eliminate solid acid catalyst and then chromatographed on silica gel. Spectral and physico-chemical data for 1, 3 and 4-6 (α,β) are proposed in Supplementary Data S4. i-Propyl d-glucofuranosidurono-6,3-lactone 7: White solid (recrystallised in CHCl3); mp 110-112 °C (decomp.). IR (KBr) ν 3440 cm-1, 2976 cm-1, 1755 cm-1. Compound 7β: TLC (EtOAc/n-hexane 1/1 v/v): Rf 0.11. 1H NMR (600 MHz, D2O) δ 5.17 (s, 1H, H-1), 4.88 (m, 2H, H-3, H-4), 4.59 (d, 1H, J4,5 6.6 Hz, H-5), 4.21 (s, 1H, H-2), 3.87 (m, 1H, OCH(CH3)2), 1.17 (d, 6H, OCH(CH3)2). 13C NMR (D2O) δ 177.23 (C{double bond, long}O), 107.66 (C-1), 83.79 (C-3), 76.79 (C-4), 76.69 (C-2), 69.03 (C-5), 64.25 (OCH(CH3)2), 23.59 (OCH(CH3)2).