Convenient Regioselective Formation of 2′-O-Tosyladenosine

Abstract

2′-O-Tosyladenosine (1) was obtained in 50% yield from the reaction of adenosine and sodium p-toluenesulfinate in the presence of sodium hypochlorite. The sequential intermediacy of N⁶−monochloroadenosine (2) and p-toluenesulfonyl chloride during this process is proposed on the basis of their individual reactions with sodium ptoluenesulfinate and adenosine, respectively.