Abstract
Tris[bis(triphenylphosphoranylidene)ammonium] pyrophosphate (PPN pyrophosphate) was used in the SN2 displacements of the tosylate ion from 5’-tosylnucleosides to afford nucleoside-5’-diphosphates. Selective precipitation permitted the direct isolation of nucleoside-5’-diphosphates from crude reaction mixtures.
Highlights
Nucleoside-5'-phosphates are key to many mechanistic studies and chemical biology applications [1,2,3]
We have recently reported the successful synthesis of PPN pyrophosphate (Scheme 1) and its application in the syntheses of nucleoside-5’-triphosphates (NTPs) [11]
The reaction progress was monitored via 31P NMR spectroscopy, and ~62% conversion to TDP 2a was attained after 30 h of reaction based on pyrophosphate consumption
Summary
Nucleoside-5'-phosphates are key to many mechanistic studies and chemical biology applications [1,2,3]. Thereafter, we consider the removal of the PPN cation from reaction mixtures alongside removal of excess pyrophosphate to facilitate the isolation of NDP products. We believe that our use of PPN pyrophosphate supports the use of elevated temperatures because it limits (or even eliminates) the possibility of water ingress into reaction mixtures and the resulting hydrolysis processes that lead to the formation of monophosphate byproducts.
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