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Communication | Special issue | Vol 13, No. 1, 1979, pp.181-185
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0181
Regioselective Phenylcarbamoylation of the Hydroxyl Groups of Purine and Pyrimidine Ribonucleosides with Bis(tributyltin)Oxide-Phenyl Isocyanate

Yoshiharu Ishido,* Ichiro Hirao, Nobuo Sakairi, and Younosuke Araki

*Department of Chemistry, Faculty of Science, Tokyo Instituteof Technology, Meguro-ku, Tokyo 152-8552, Japan


N6-Benzyladenosine (1) was found to give the corresponding 5’-phenylcarbamate (2) (83% yield) by treating with (Bu3Sn)2O in toluene under reflux and then with phenyl isocyanate at room temperature (Procedure A), and to give the corresponding 3’- (73% yield) and 2’-phenylcarbamate (10% yield) by treating with (Bu3Sn)2O and PhNCO in toluene - DMF (10:1, v/v) at 0°C (Procedure B). The procedure B was also successful in the partial phenylcarbamoylation of N6-benzoyladenosine (11), inosine (12) and uridine (13), giving the corresponding 3’-phenylcarbamates (60%, 67%, and 55% yields) and 2’-phenylcarbamates (17%, 31%, and 15% yields), respectively. On the other hand, thymidine (14) (2’-deoxyribonucleoside) afforded the corresponding 5’-phenylcarbamate (93% yield) through the procedure B.