Related Experiment Video
Updated: Jul 30, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189
Bryon Simmons1, Zhuqing Liu1, Artis Klapars1
1Department of Process Chemistry, Merck & Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
Abstract:
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.
Related Concept Videos
Inhibitors of Bacterial DNA Synthesis
Inhibitors of Viral Protein Synthesis
Antiviral Nucleoside Inhibitors
Inhibitors of Virion Maturation and Assembly

