Alkoxylation and Phosphorylation of Pyrimidine Disulfides: Green Synthesis of Alkoxypyrimidine Thioethers and Pyrimidine Phosphorothioates

This paper addresses a novel, green, and sustainable method to construct new C–S and P–S bonds by cleaving the S–S bond in pyrimidine disulfide under various conditions. The first alkoxylation and phosphorylation of pyrimidine disulfide are effectively accomplished by this approach. Compared to the methods reported, this approach provides more benefits, including the utilization of eco-friendly solvents, straightforward procedure, mild reaction conditions, high atomic efficiency, and a broad range of applicable substrates. As a result, we were able to synthesize a variety of pyrimidine phosphorothioate lipids with potential applications. Furthermore, a series of control experiments as well as theoretical calculations are performed in this work to produce deeper insights of the transfer mechanism.