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Studies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer

 

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Opened Access Studies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer
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Author: Moya López, Juan Francisco
Elhalem, Eleonora
Recio Jiménez, Rocío
Álvarez González, Eleuterio
Fernández Fernández, Inmaculada
Khiar, Noureddine
Department: Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica
Date: 2015
Published in: Organic and Biomolecular Chemistry, 13 (6), 1904-1914.
Document type: Article
Abstract: A detailed study on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides is reported. It has been shown that the sense and the degree of stereochemical outcome of the oxidation are highly depen- dent on the substituent of the sulfur and on the protective group of the C2–OH. In the case of thioglyco-sides with a bulky aglycone, the mesylation of C2–OH has a significant effect on the stereochemical outcome of the oxidation, affording the usually less favoured RS sulfoxide as a single diastereoisomer. The absolute configuration of the final sulfinyl glycosides was ascertained by NMR analysis and corroborated by X-ray crystallography.
Cite: Moya López, J.F., Elhalem, E., Recio Jiménez, R., Álvarez González, E., Fernández Fernández, I. y Khiar, N. (2015). Studies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer. Organic and Biomolecular Chemistry, 13 (6), 1904-1914.
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URI: http://hdl.handle.net/11441/42500

DOI: 10.1039/c4ob02030h

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