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

Autores
Elhalem, Eleonora; Comin, Maria Julieta; Rodriguez, Juan Bautista
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
6-Thiabicyclo[3.1.0]Hexane
Carbanucleosides
Nucleosides
Thiiranes 2″,3″-Dideoxyneplanocin C
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/70607
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogateElhalem, EleonoraComin, Maria JulietaRodriguez, Juan Bautista6-Thiabicyclo[3.1.0]HexaneCarbanucleosidesNucleosidesThiiranes 2″,3″-Dideoxyneplanocin Chttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The 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, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaWiley VCH Verlag2006-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/70607Elhalem, Eleonora; Comin, Maria Julieta; Rodriguez, Juan Bautista; Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate; Wiley VCH Verlag; European Journal of Organic Chemistry; 19; 9-2006; 4473-44821434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200600488info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200600488info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:46:33Zoai:ri.conicet.gov.ar:11336/70607instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:46:34.217CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
title Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
spellingShingle Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
Elhalem, Eleonora
6-Thiabicyclo[3.1.0]Hexane
Carbanucleosides
Nucleosides
Thiiranes 2″,3″-Dideoxyneplanocin C
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
dc.creator.none.fl_str_mv Elhalem, Eleonora
Comin, Maria Julieta
Rodriguez, Juan Bautista
author Elhalem, Eleonora
author_facet Elhalem, Eleonora
Comin, Maria Julieta
Rodriguez, Juan Bautista
author_role author
author2 Comin, Maria Julieta
Rodriguez, Juan Bautista
author2_role author
author
dc.subject.none.fl_str_mv 6-Thiabicyclo[3.1.0]Hexane
Carbanucleosides
Nucleosides
Thiiranes 2″,3″-Dideoxyneplanocin C
topic 6-Thiabicyclo[3.1.0]Hexane
Carbanucleosides
Nucleosides
Thiiranes 2″,3″-Dideoxyneplanocin C
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
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.
publishDate 2006
dc.date.none.fl_str_mv 2006-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/70607
Elhalem, Eleonora; Comin, Maria Julieta; Rodriguez, Juan Bautista; Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate; Wiley VCH Verlag; European Journal of Organic Chemistry; 19; 9-2006; 4473-4482
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/70607
identifier_str_mv Elhalem, Eleonora; Comin, Maria Julieta; Rodriguez, Juan Bautista; Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate; Wiley VCH Verlag; European Journal of Organic Chemistry; 19; 9-2006; 4473-4482
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200600488
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200600488
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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