Syntheses of N4,2',3',5'-tetraacylcytidines from N4-acylcytosines, via condensation with tetraacylribose and transribosylation with acylated purine nucleosides.

Abstract

N4-Isobutyryl- and -(2-ethylhexanoyl)cytosines (Ia, b) were synthesized by acylation of cytosine. N4, 2', 3', 5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involeves condensation of N4-acylcytosines (I) and 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N4-acylcytosines and acyl-inosines or -guanosines (IVa-d). N4-Octanoyl-2', 3', 5'-triacetylcytidine (IIIf) waS converted into cytidine by deacylation in a good yield.