Studies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer
| Autor: | Inmaculada Fernández, Eleonora Elhalem, Rocío Recio, Eleuterio Álvarez, Noureddine Khiar, Juan Francisco Moya-López |
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| Přispěvatelé: | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica, Ministerio de Economía y Competitividad (MINECO). España, Junta de Andalucía |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Models
Molecular chemistry.chemical_classification Crystallography Stereochemistry Organic Chemistry Molecular Conformation Diastereomer Substituent Absolute configuration Thio Glycoside Stereoisomerism Stereoselectivity Sulfoxide Crystallography X-Ray Biochemistry chemistry.chemical_compound Aglycone chemistry Thioglycosides Safrole Oxidation Physical and Theoretical Chemistry Oxidation-Reduction |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname idUS. Depósito de Investigación de la Universidad de Sevilla |
| Popis: | 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 dependent on the substituent of the sulfur and on the protective group of the C2–OH. In the case of thioglycosides 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. |
| Databáze: | OpenAIRE |
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