An Improved Transient Method for the Synthesis of N-Benzoylated Nucleosides

Abstract

The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCl) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

Keywords:

• Transient method
• N-benzoylation
• Protection
• Nucleosides

Acknowledgments

This work was supported by grants from the Texas Advanced Technology Research Program and the Robert A. Welch Foundation. We thank Dr. Clotilde Pichon-Santander for helpful discussion.