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Issue 8, 2009
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Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

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Abstract

Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

Graphical abstract: Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

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Article information


Submitted
10 Mar 2009
Accepted
23 Apr 2009
First published
18 May 2009

Green Chem., 2009,11, 1179-1183
Article type
Paper

Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

J. Augé and G. Sizun, Green Chem., 2009, 11, 1179
DOI: 10.1039/B904692E

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