Article
Studies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer
Author/s | 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 |
Publication Date | 2015 |
Deposit Date | 2016-06-21 |
Published in |
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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 ... 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. |
Funding agencies | Ministerio de Economía y Competitividad (MINECO). España Junta de Andalucía |
Project ID. | info:eu-repo/grantAgreement/MINECO/CTQ2010-21755-CO2-01
![]() CTQ2010- 21755-CO2-01 ![]() info:eu-repo/grantAgreement/MINECO/CTQ2013-49066-C2-1-R ![]() info:eu-repo/grantAgreement/MINECO/CTQ2013-49066-C2-2-R ![]() P11-FQM-8046 ![]() |
Citation | 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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