Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group.

ABSTRACT

We report the synthesis and properties of nucleoside derivatives acylated by 2-(trimethylsilyl)benzoyl (TMSBz) that proved to be extremely stable under basic conditions when introduced into the 5'-hydroxyl group of thymidine, the 4-amino group of deoxycytidine and the 2'-hydroxyl group of uridine. In particular, 2'-O-TMSBz-uridine could be isolated and was more stable in pyridine, while it isomerized in CH(2)Cl(2) in the presence of Et(3)N to yield a mixture of the 2'-O- and 3'-O-acylated species.