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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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
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spelling todo:paper_1434193X_v_n3_p540_Repetto2023-10-03T16:14:18Z Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end Repetto, E. Marino, C. Uhrig, M.L. Varela, O. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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
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
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.
format JOUR
author Repetto, E.
Marino, C.
Uhrig, M.L.
Varela, O.
author_facet Repetto, E.
Marino, C.
Uhrig, M.L.
Varela, O.
author_sort Repetto, E.
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
url http://hdl.handle.net/20.500.12110/paper_1434193X_v_n3_p540_Repetto
work_keys_str_mv AT repettoe twostraightforwardstrategiesforthesynthesisofthiodisaccharideswithafuranoseunitasthenonreducingend
AT marinoc twostraightforwardstrategiesforthesynthesisofthiodisaccharideswithafuranoseunitasthenonreducingend
AT uhrigml twostraightforwardstrategiesforthesynthesisofthiodisaccharideswithafuranoseunitasthenonreducingend
AT varelao twostraightforwardstrategiesforthesynthesisofthiodisaccharideswithafuranoseunitasthenonreducingend
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