Collect. Czech. Chem. Commun. 2010, 75, 33-57
Published online 2010-02-08 13:36:33

A convenient protection for 4-oxopyrimidine moieties in nucleosides by the pivaloyl group

Michał Sobkowski

Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland


Application of the pivaloyl group as a protection for the N3 position of thymidine and uridine was investigated. Pivaloylation of thymidine is a very rapid reaction proceeding under mild conditions with excellent regioselectivity for sugar or thymine moiety, depending on the amines used. Several pivaloylated thymidine derivatives were obtained by treatment of unprotected thymidine with pivaloyl chloride under various experimental conditions. Stability of the N3-pivaloyl protecting group under basic and acidic conditions was evaluated and the conditions for its selective removal were found.

Keywords: Thymidine; Uridine; Pivaloyl; Acylations; Protecting groups; Regioselectivity.

References: 67 live references.