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
Hauptverfasser: Blade, Helen, Bradley, Derek, Diorazio, Louis, Evans, Timothy, Hayter, Barry R, Howell, Gareth P
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00607