124130-15-0Relevant academic research and scientific papers
New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation
Maguire, Anita R.,Hladezuk, Isabelle,Ford, Alan
, p. 369 - 372 (2002)
An improved procedure for the synthesis of N-benzoyl-2′,3′-O-isopropylidene uridine via one-step selective N-benzoylation of 2′,3′-O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described. De-N-benzoylation of N-benzoylated thymidine and uridine derivatives can be conveniently effected under neutral conditions, by heating with benzyl alcohol.
A convenient protection for 4-oxopyrimidine moieties in nucleosides by the pivaloyl group
Sobkowski, Michal
experimental part, p. 33 - 57 (2010/07/05)
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.
