REACTION OF PHENYLBORONIC ACID WITH NUCLEOSIDES AND MONONUCLEOTIDES

2′,3′-O-Phenylboronates of adenosine (I), uridine (II), inosine (III) and cytidine (IV) have been prepared from corresponding nucleosides and phenylboronic acid (PBA). The protecting group can be removed with propane-1,3-diol under mild conditions in anhydrous medium. On heating 2′(3′)-monophosphates of adenosine and cytidine with PBA a specific dephosphorylation was achieved leading to 2′,3′-phenylboronates (I, IV). The synthetic aspects of the application of nucleoside phenylboronic esters (tritylation, tosylation and phosphorylation) have been studied. © 1969.