Artículo
Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
Fecha de publicación:
09/2006
Editorial:
Wiley VCH Verlag
Revista:
European Journal of Organic Chemistry
ISSN:
1434-193X
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
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Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Citación
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
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