Nucleotide phosphorothioates have been identified as potential anticancer, antiviral and antimicrobial agents, but their synthesis has been proven challenging. The process development for 2'F-adenosine-5'-monothiophosphate will be described. Kinetic profiling, NMR monitoring, investigation of product decomposition pathways, and crystallization control identified the important parameters for an efficient thiophosphorylation process. Among those identified parameters are the use of pivaloyl as the protecting group for the nucleoside starting material as well as the use of triethylphosphate as a green reaction solvent, both of which are critical for allowing a homogeneous reaction mixture and key to the success of the large scale reaction.

Process development for 2'F-adenosine-5'-monothiophosphat

ACS Spring Meeting 2021

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