3 years ago

Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189

Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189
Steven M. Silverman, Artis Klapars, Bryon Simmons, Zhuqing Liu, Ana Bellomo
A general and efficient method for the synthesis of pronucleotide (ProTide) 5′-phosphoramidate monoesters is reported. This method consists of a highly stereoselective 5′-phosphorylation mediated by dimethylaluminum chloride to afford the desired target ProTides in excellent yields without employing 3′-protection strategies. The application of this methodology to the synthesis of a number of pharmaceutically relevant compounds currently marketed or under investigation in clinical research is demonstrated.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00469

DOI: 10.1021/acs.orglett.7b00469

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