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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2006
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Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n19_p4473_Elhalem http://hdl.handle.net/20.500.12110/paper_1434193X_v_n19_p4473_Elhalem |
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paper:paper_1434193X_v_n19_p4473_Elhalem2023-06-08T16:14:23Z Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate Elhalem, Eleonora Comin, María Julieta Rodríguez, Juan Bautista 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. 2006 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n19_p4473_Elhalem 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, Eleonora Comin, María Julieta Rodríguez, Juan Bautista 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. |
author |
Elhalem, Eleonora Comin, María Julieta Rodríguez, Juan Bautista |
author_facet |
Elhalem, Eleonora Comin, María Julieta Rodríguez, Juan Bautista |
author_sort |
Elhalem, Eleonora |
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 |
publishDate |
2006 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n19_p4473_Elhalem http://hdl.handle.net/20.500.12110/paper_1434193X_v_n19_p4473_Elhalem |
work_keys_str_mv |
AT elhalemeleonora synthesisofconformationallylockedcarbocyclicnucleosidesbuiltonathiabicyclo310hexanesystemasapseudosugarsurrogate AT cominmariajulieta synthesisofconformationallylockedcarbocyclicnucleosidesbuiltonathiabicyclo310hexanesystemasapseudosugarsurrogate AT rodriguezjuanbautista synthesisofconformationallylockedcarbocyclicnucleosidesbuiltonathiabicyclo310hexanesystemasapseudosugarsurrogate |
_version_ |
1768545571408183296 |