Hristo Petrov Daskalov, Mitsuo Sekine, Tsujiaki Hata
1981
Citations
0
Influential Citations
35
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Reactions of 2′,3′,5′-tri-O-acetyl-N2-protected or unprotected guanosine derivatives with phosphoryl, phosphinothioyl, arylsulfonyl, and silyl halides in dichloromethane gave the corresponding O6-substituted guanosine derivatives in good yields. In these reactions, 4-(dimethylamino)pyridine (DMAP) was found to be very effective catalyst. The physical data of these products and their stabilities under acidic and basic conditions were described in detail. Selective detritylation of O6-arylsulfonyl-N2-tritylguanosine derivatives was accomplished by treatment with 80% acetic acid. It was found that O6-dibutylphosphinothioyl derivatives were relatively stable under conditions where acetyl group was predominantly removed.