Synthesis of adenosine cyclic 3′,5′ -phosphorofuoridate (camp-f)

Article abstract of DOI:10.1016/0040-4039(95)01691-A

Work aimed at the chiral synthesis of both diastereomers of adenosine cyclic 3′,5′phosphorofluoridate, cAMP-F 7, is described. Attempted debenzoylation of the intermediate N⁶,N⁶,O_2′tribenzoyladenosine cyclic 3′,5′-phosphorofluoridate 4 by ammonolysis resulted in cleavage of the P-F bond. Reaction of [Sp]-S-methyl adenosine 3′,5′-cyclophosphorothioate 6 with AgF gives a mixture of the two diastereoisomers of the cyclic phosphore fluoridate 7 along with adenosine 2′ ,3′-cyclic phosphate 8. The conversion of 7 into 8 can be completed under remarkably mild conditions. Possible mechanisms for this unusual transformation are discussed.