Collect. Czech. Chem. Commun. 1988, 53, 1568-1573

Preparation and some reactions of bis(2',3'-O-carbonyl-6-azauridine) 5',5''-carbonate

Pavel Drašar and Jiří Beránek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of 6-azauridine (I) with phosgene and hexamethylphosphoramide afforded the title compound II. Both its 2',3'-cyclic carbonate groups were selectively deblocked with methanolic sodium methoxide under preservation of the internucleoside carbonate bridge. The carbonate II was also converted into the 5',5''-carbonyloxybis(2,2'-anhydro) derivative III by heating with imidazole in N,N-dimethylformamide. Several analogues of II were prepared by reaction of 1,1'-carbonyldiimidazole with the corresponding nucleosides in N,N- dimethylformamide.