New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for
Anita R Maguire1, Isabelle Hladezuk, Alan Ford
1Department of Chemistry, University College Cork, Cork, Ireland. a.r.maguire@ucc.ie
Abstract:
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.
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Biosynthesis of Nucleic Acids
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of Nitriles

