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

Moya López, Juan FranciscoElhalem, EleonoraRecio Jiménez, RocíoÁlvarez González, EleuterioFernández Fernández, InmaculadaKhiar, Noureddine2016-06-212016-06-212015Moya 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), 1904-1914.1477-0520http://hdl.handle.net/11441/42500A 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.application/pdfengAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/CrystallographyOxidationStereoselectivityStudies on the diastereoselective oxidation of 1-thio-β-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomerinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccesshttps://doi.org/10.1039/c4ob02030h