Synthesis of Three Regioisomeric (7-Methoxychromenonyl)methyl Guanosine 5′-Phosphates

Abstract

Herein we describe the synthesis of three new (7-methoxychromenonyl)methyl 2-N-propionyl-2′,3′-isopropylideneguanosine 5′-phosphate diesters, potentially photolabile nucleotides, via an H-phosphonate strategy. The stability of these compounds toward acidic and basic conditions was evaluated during the nucleoside moiety deprotection.

Keywords:

• Chromenone
• guanosine
• H-phosphonate
• 5′-monophosphate
• nucleotide
• phosphate diester

ACKNOWLEDGMENTS

E F.-P. is grateful to Ecole Doctorale du Médicament (EDM) for a three-year doctoral fellowship. K.Y., a visiting student at Paris Descartes in 2007, is grateful both to the University of Okayama (from Pr. H. Tanaka's group at School of Engineering) for a leave of absence and to Paris Descartes University (Service des Relations Internationales) for partial financial support during his stay in Paris. The authors also acknowledge funding from the French Centre National de la Recherche Scientifique (CNRS) and Paris Descartes University.