Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs

Abstract: This thesis focuses on chemical transformations of H-phosphonate and H-phosphonothioate and can be divided in two parts. The first part, is devoted to the development of the palladium-catalyzed P-C bond formation. Both mechanistic and synthetic studies of the transformations have been performed. The stereochemical aspects of palladium catalyzed arylation and benzylation of DNA analogs containing H-phosphonate and H-phosphonothioate have been studied.In chapter 5 the condensation using Mitsunobu reaction of H-phosphonate function and nucleoside has been studied. Efficient protocols for the synthesis of nucleoside H-phosphonate monoester were developed.The last chapter deals with development of silylation-mediated transesterfication of phenyl H-phosphonothioate as a thiophosphonylating agent. The methodology was used to prepare nucleoside H-phosphonothioate monomeric building blocks in good yields.