Adenosine dialdehyde analogs I: Regioselective synthesis of adenosine monoaldehydes

Selective borohydride reduction of adenosine dialdehyde (1) gave the known adenosine 2′-monoaldehyde (2). Reaction of 1 with N,N′-diphenylethylenediamine, followed by reduction and deblocking gave adenosine 3′-monoaldehyde (5), a new compound. Unlike 2, compound 5 inhibited S-AdoHcy hydrolase and showed antiviral activity in vitro.