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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Guardado en:
Detalles Bibliográficos
Publicado: 2008
Materias:
Catalysis
Furanose
Glycosylation
Michael addition
Molybdenum
Thiodisaccharides
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n3_p540_Repetto
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
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spelling paper:paper_1434193X_v_n3_p540_Repetto2025-07-30T18:50:11Z Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end Catalysis Furanose Glycosylation Michael addition Molybdenum Thiodisaccharides 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. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n3_p540_Repetto http://hdl.handle.net/20.500.12110/paper_1434193X_v_n3_p540_Repetto
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Catalysis
Furanose
Glycosylation
Michael addition
Molybdenum
Thiodisaccharides
spellingShingle Catalysis
Furanose
Glycosylation
Michael addition
Molybdenum
Thiodisaccharides
Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
topic_facet Catalysis
Furanose
Glycosylation
Michael addition
Molybdenum
Thiodisaccharides
description 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.
title Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
title_short Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
title_full Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
title_fullStr Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
title_full_unstemmed Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
title_sort two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end
publishDate 2008
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n3_p540_Repetto
http://hdl.handle.net/20.500.12110/paper_1434193X_v_n3_p540_Repetto
_version_ 1840323043982835712

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