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Abstract:

Thiodisaccharides having a 1-thiopentofuranose nonreducing end were synthesized by two routes starting from per-O-acylaldofuranoses with arabino, ribo, and xylo configurations. These glycosyl donors were converted into S-glycosyl isothiourea derivatives as precursors of 1-thiofuranose units, which were generated in situ and trapped by a sugar enone to produce, by Michael addition, the thioglycosidic linkage. Alternatively, the MoO2Cl 2-promoted glycosylation of the thiol group of 6-thiosugar derivatives by per-O-acylfuranose led to thiodisaccharides with exclusive 1,2-trans diastereocontrol. © Wiley-VCH Verlag GmbH & Co. KGaA.

Registro:

Documento: Artículo
Título:Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
Autor:Repetto, E.; Marino, C.; Uhrig, M.L.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Catalysis; Furanose; Glycosylation; Michael addition; Molybdenum; Thiodisaccharides
Año:2008
Número:3
Página de inicio:540
Página de fin:547
DOI: http://dx.doi.org/10.1002/ejoc.200700874
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n3_p540_Repetto

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Citas:

---------- APA ----------
Repetto, E., Marino, C., Uhrig, M.L. & Varela, O. (2008) . Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end. European Journal of Organic Chemistry(3), 540-547.
http://dx.doi.org/10.1002/ejoc.200700874
---------- CHICAGO ----------
Repetto, E., Marino, C., Uhrig, M.L., Varela, O. "Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end" . European Journal of Organic Chemistry, no. 3 (2008) : 540-547.
http://dx.doi.org/10.1002/ejoc.200700874
---------- MLA ----------
Repetto, E., Marino, C., Uhrig, M.L., Varela, O. "Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end" . European Journal of Organic Chemistry, no. 3, 2008, pp. 540-547.
http://dx.doi.org/10.1002/ejoc.200700874
---------- VANCOUVER ----------
Repetto, E., Marino, C., Uhrig, M.L., Varela, O. Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end. Eur. J. Org. Chem. 2008(3):540-547.
http://dx.doi.org/10.1002/ejoc.200700874