Unlocking new pathways to a 3',5'-phosphoroselenolate-dinucleotide m7G cap precursor, β-E-vinyl pinacol boronates and to 2-benzosilolines

Significantly, the newly developed route has introduced a substantial amount of new synthetic methodology, seen for the first time ever. Some notable highlights include the application of the Michaelis-Arbuzov ligation reaction to sterically hindered 3ʹ-H-phosphonate ribonucleotide systems, the first solution-phase application of the solid CPR II reagent in the 5ʹ-O-phosphorylation of oligonucleotides, and the first successful use of 70% wt. aqueous t-BuO2H to oxidise a nucleoside trialkoxy phosphite into its corresponding O-phosphate ester in the presence of readily oxidisable selenomethyl ether and phosphoroselenolate functionality.

Chapter 1 also discloses a new, reliable synthetic method for the acquisition of a range of C2ʹ-modified adenosines; intermediates which could prove valuable for gaining access to other C2ʹ-modified m7G caps and a variety of C2ʹ-modified mRNAs in the near future.<br><br>Chapter 2 reports on the use of a new PtCl2/XPhos/Et3SiH catalyst system for hydroborating a wide range of heteroatom-functionalised terminal alkynes with pinacolborane.