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Abstract:

Since the enantio or diastereoselective preparation of sulfoxides is a current challenge, we explore the possibility of inducing diastereoselectivity in the oxidation of the sulfur atom of thiodisaccharides, according to their substitution patterns. Thus, a series of 3-deoxy-4-S-(β-d-glucopyranosyl)-4-thio-β-d-xylo-hexopyranoside derivatives, with different substituents at C-6 (OH, OAc or OTBS) of the reducing end, have been synthesized and treated with m-CPBA for the oxidation of the sulfur atom at C-4, which is vicinal to C-6. The absolute configuration at the sulfur stereocenter of the resulting sulfoxides was established taking into account shielding/deshielding anisotropic effects of the SO bond on the chemical shift of the NMR signals of selected protons, in the most populated syn φ/syn ψ conformation of the thiodisaccharide S-oxides. The OAc and OTBS derivatives afforded diastereomeric mixtures of R and S sulfoxides in a similar ratio (1.4 : 1 and 1.6 : 1, respectively). In contrast, the oxidation of thiodisaccharide with a free hydroxyl group at C-6 was completely diastereoselective in favor of the R sulfoxide. The influence of the thiodisaccharide C-6 substituent on the stereochemical course of the oxidation is discussed. © 2017 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides
Autor:Colomer, J.P.; Peñéñory, A.B.; Varela, O.
Filiación:Instituto de Investigaciones en Fisico-Quimica de Cordoba-Universidad Nacional de Cordoba, Facultad de Ciencias Químicas, Departamento de Química Orgánica, Edificio de Ciencias 2, Ciudad Universitaria, Córdoba, CP5016, Argentina
Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, Buenos Aires, C1428EHA, Argentina
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET)-UBA, Centro de Investigación en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina
Palabras clave:Atoms; Chemical shift; Oxidation; Stereoselectivity; Sulfur; Absolute configuration; Anisotropic effects; Asymmetric induction; Diastereo-selectivity; Diastereoselective; Free hydroxyl groups; Oxidation reactions; Substitution patterns; Internal oxidation
Año:2017
Volumen:7
Número:70
Página de inicio:44410
Página de fin:44420
DOI: http://dx.doi.org/10.1039/c7ra07225b
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v7_n70_p44410_Colomer

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Citas:

---------- APA ----------
Colomer, J.P., Peñéñory, A.B. & Varela, O. (2017) . Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides. RSC Advances, 7(70), 44410-44420.
http://dx.doi.org/10.1039/c7ra07225b
---------- CHICAGO ----------
Colomer, J.P., Peñéñory, A.B., Varela, O. "Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides" . RSC Advances 7, no. 70 (2017) : 44410-44420.
http://dx.doi.org/10.1039/c7ra07225b
---------- MLA ----------
Colomer, J.P., Peñéñory, A.B., Varela, O. "Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides" . RSC Advances, vol. 7, no. 70, 2017, pp. 44410-44420.
http://dx.doi.org/10.1039/c7ra07225b
---------- VANCOUVER ----------
Colomer, J.P., Peñéñory, A.B., Varela, O. Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides. RSC Adv. 2017;7(70):44410-44420.
http://dx.doi.org/10.1039/c7ra07225b