Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate

The synthesis of prototype models of purine and pyrimidine carbanucleosides built on a 6-thiabicyclo[3.1.0]hexane system as pseudosugar moiety has been investigated. These pyrimidine carbanucleosides proved to be very stable compounds, in contrast to the parent epoxy analogs, which experienced epoxi...

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Autores principales: Elhalem, E., Comin, M.J., Rodriguez, J.B.
Formato: JOUR
Materias:
6-Thiabicyclo[3.1.0]hexane
Carbanucleosides
Nucleosides
Thiiranes 2′,3′-Dideoxyneplanocin C
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_1434193X_v_n19_p4473_Elhalem
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_1434193X_v_n19_p4473_Elhalem2023-10-03T16:14:16Z Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate Elhalem, E. Comin, M.J. Rodriguez, J.B. 6-Thiabicyclo[3.1.0]hexane Carbanucleosides Nucleosides Thiiranes 2′,3′-Dideoxyneplanocin C The synthesis of prototype models of purine and pyrimidine carbanucleosides built on a 6-thiabicyclo[3.1.0]hexane system as pseudosugar moiety has been investigated. These pyrimidine carbanucleosides proved to be very stable compounds, in contrast to the parent epoxy analogs, which experienced epoxide ring-opening due to intramolecular enol base attack. In addition, as the synthesis of a thiirane moiety fused to a five-membered ring is not a trivial synthetic task, validation and optimization of the existing methods for episulfide preparation were required to access the committed synthetic precursor of the title compounds: (±)-(1RS,2RS,5SR)-6-thiabicyclo[3.1.0]hexan-2- ol, compound 28. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006. Fil:Elhalem, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Comin, M.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Rodriguez, J.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1434193X_v_n19_p4473_Elhalem
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 6-Thiabicyclo[3.1.0]hexane
Carbanucleosides
Nucleosides
Thiiranes 2′,3′-Dideoxyneplanocin C
spellingShingle 6-Thiabicyclo[3.1.0]hexane
Carbanucleosides
Nucleosides
Thiiranes 2′,3′-Dideoxyneplanocin C
Elhalem, E.
Comin, M.J.
Rodriguez, J.B.
Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
topic_facet 6-Thiabicyclo[3.1.0]hexane
Carbanucleosides
Nucleosides
Thiiranes 2′,3′-Dideoxyneplanocin C
description The synthesis of prototype models of purine and pyrimidine carbanucleosides built on a 6-thiabicyclo[3.1.0]hexane system as pseudosugar moiety has been investigated. These pyrimidine carbanucleosides proved to be very stable compounds, in contrast to the parent epoxy analogs, which experienced epoxide ring-opening due to intramolecular enol base attack. In addition, as the synthesis of a thiirane moiety fused to a five-membered ring is not a trivial synthetic task, validation and optimization of the existing methods for episulfide preparation were required to access the committed synthetic precursor of the title compounds: (±)-(1RS,2RS,5SR)-6-thiabicyclo[3.1.0]hexan-2- ol, compound 28. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
format JOUR
author Elhalem, E.
Comin, M.J.
Rodriguez, J.B.
author_facet Elhalem, E.
Comin, M.J.
Rodriguez, J.B.
author_sort Elhalem, E.
title Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title_short Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title_full Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title_fullStr Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title_full_unstemmed Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title_sort synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
url http://hdl.handle.net/20.500.12110/paper_1434193X_v_n19_p4473_Elhalem
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AT cominmj synthesisofconformationallylockedcarbocyclicnucleosidesbuiltonathiabicyclo310hexanesystemasapseudosugarsurrogate
AT rodriguezjb synthesisofconformationallylockedcarbocyclicnucleosidesbuiltonathiabicyclo310hexanesystemasapseudosugarsurrogate
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