Modular Synthesis of Constrained Ethyl (cEt) Purine and Pyrimidine Nucleosides
A modular and scalable approach to pyrimidine- and purine-containing constrained ethyl (cEt) nucleosides is demonstrated. Minimizing stereochemical adjustments and protecting group manipulations, diacetone glucose is converted to two representative cEt nucleosides via a functionalized, common interm...
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Veröffentlicht in: | Journal of organic chemistry 2015-05, Vol.80 (10), p.5337-5343 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | A modular and scalable approach to pyrimidine- and purine-containing constrained ethyl (cEt) nucleosides is demonstrated. Minimizing stereochemical adjustments and protecting group manipulations, diacetone glucose is converted to two representative cEt nucleosides via a functionalized, common intermediate. The retrosynthetic approach to this complex class of drug precursors offers clear benefits over existing routes based on step count and efficiency. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.5b00607 |