Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines

[Image: see text] A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp(2)–sp, sp(2)–sp(2), and sp(2)–sp(3) cross-couplin...

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Detalles Bibliográficos
Autores principales: Weseliński, Łukasz J., Begoyan, Vagarshak, Ferrier, Alexis, Tanasova, Marina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6045343/
https://www.ncbi.nlm.nih.gov/pubmed/30023537
http://dx.doi.org/10.1021/acsomega.7b01159
Descripción
Sumario:[Image: see text] A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp(2)–sp, sp(2)–sp(2), and sp(2)–sp(3) cross-coupling conditions for modification of 3-deazaadenine to access C3-modified adenine and hypoxanthine scaffolds. The optimized methodologies to access the corresponding 3-deazaadenosine phosphoramidites for solid-phase DNA synthesis have been demonstrated.

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