Synthesis of Certain 2′-Deoxy-3′,5′-di-O-benzyl-4′-thio-nucleosides Using Natural Phosphate Doped with Trifluoromethanesulfonic Acid as Catalyst

Abstract

A series of 2′-deoxy-4′-thionucleosides are synthesized by coupling 1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentufuranose to trimethylsilylated nucleobases using natural phosphate doped with trifluoromethanesulfonic acid as catalyst. The detail of this one-pot method and the comparison between the percentage of α and β -2′-deoxy-4′-thionucleosides with those described previously are also reported.

Keywords:

• 2′-Deoxy-3′,5′-di-O-benzyl-4′-thionucleosides
• natural phosphate
• trifluoromethanesulfonic acid

Acknowledgments

This investigation was supported by University Cadi Ayyad Marrakesh, Morocco; CNRST (Rabat Morocco); and by National Institute of Health (P01-CA34200). H.B.L. thanks all colleagues in the Drug Discovery Division (SRI) for their help. The authors are indebted to Dr. James M. Riordan, Mr. Mark Richardson, Ms. J. Truss, and Ms. Joan Bearden for spectral data and MS.

Notes

*The yield was calculated after purification on chromatography column.