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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
Autor:Elhalem, E.; Comin, M.J.; Rodriguez, J.B.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, C1428EHA, Buenos Aires, Argentina
Palabras clave:6-Thiabicyclo[3.1.0]hexane; Carbanucleosides; Nucleosides; Thiiranes 2′,3′-Dideoxyneplanocin C
Año:2006
Número:19
Página de inicio:4473
Página de fin:4482
DOI: http://dx.doi.org/10.1002/ejoc.200600488
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n19_p4473_Elhalem

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  • note

Citas:

---------- APA ----------
Elhalem, E., Comin, M.J. & Rodriguez, J.B. (2006) . Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate. European Journal of Organic Chemistry(19), 4473-4482.
http://dx.doi.org/10.1002/ejoc.200600488
---------- CHICAGO ----------
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" . European Journal of Organic Chemistry, no. 19 (2006) : 4473-4482.
http://dx.doi.org/10.1002/ejoc.200600488
---------- MLA ----------
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" . European Journal of Organic Chemistry, no. 19, 2006, pp. 4473-4482.
http://dx.doi.org/10.1002/ejoc.200600488
---------- VANCOUVER ----------
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. Eur. J. Org. Chem. 2006(19):4473-4482.
http://dx.doi.org/10.1002/ejoc.200600488