Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end

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 w...

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Detalles Bibliográficos
Autores principales: Repetto, E., Marino, C., Uhrig, M.L., Varela, O.
Formato: JOUR
Materias:
Catalysis
Furanose
Glycosylation
Michael addition
Molybdenum
Thiodisaccharides
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_1434193X_v_n3_p540_Repetto
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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