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

ABSTRACT: 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 sp2-sp, sp2-sp2, and sp2-sp3 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.

SUBMITTER: Weselinski LJ

PROVIDER: S-EPMC6045343 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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

Weseliński Łukasz J ŁJ Begoyan Vagarshak V Ferrier Alexis A Tanasova Marina M

ACS omega 20171020 10

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 sp2-sp, sp2-sp2, and sp2-sp3 cross-coupling conditions for modification of 3-deazaadenine to access C3-modified adenine and hypoxanthine scaffolds. The optimized methodologies to access the corresponding 3-deazaaden ...[more]

PMID: 30023537

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