Abstract
Methylation of 3', 5'-di-O-trityluridine (I) gave a mixture of two compounds, which was detritylated and then separated to give N3, 2'-O-dimethyluridine (V) and 2'-O-methyluridine (VI). After treatment of the above mixture with ethanolic ammonia, the reaction products were detritylated and separated to give V and 2'-O-methyl-cytidine (VII). By a similar method 3'-O-methyl nucleosides were obtained from 2', 5'-di-O-trityluridine (II). The relative rates of acidic hydrolysis of uridine, VI, and 3'-O-methyluridine have been determined and were shown to obey first order kinetics. Introduction of a methoxyl function at the 2'- or 3'-position of uridine enhances the stability of the glycosyl linkage to acid hydrolysis.
