New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation.
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.
Maguire
Anita R
AR
Department of Chemistry, University College Cork, Cork, Ireland. a.r.maguire@ucc.ie
Hladezuk
Isabelle
I
Ford
Alan
A
D001565:Benzoates / Q000737:chemistry; D013936:Thymidine / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*
D001565:Benzoates; C456724:N-benzoyl-2',3'-O-isopropylidene uridine; D013936:Thymidine; C013409:benzoyl chloride; D014529:Uridine