title: Regioselective Mitsunobu Reaction of Partially Protected Uridine.
abstract: Mitsunobu reaction of partially acylated uridine proceeds with high regioselectivity for intramolecular SN2 anhydro linkage closuring. Under the reaction conditions, an isomeric mixture of diacyl uridine derivatives with either free 2'- or 3'-hydroxyl group was transformed into a single cyclonucleosidic product, 2,2'-anhydro-3',5'-di-O-acyluridine. This paper presents a possible mechanism of the reactions, the explanation of observed phenomenon based on semiempirical and density functional theory (DFT) calculations and possible utility of this synthetic pathway.
authors.affiliation: a Institute of Bioorganic Chemistry, Polish Academy of Sciences , Poznan , Poland.
authors.forename: Maurycy
authors.initials: M
authors.lastname: Szlenkier
authors.affiliation: a Institute of Bioorganic Chemistry, Polish Academy of Sciences , Poznan , Poland.
authors.forename: Karol
authors.initials: K
authors.lastname: Kamel
authors.affiliation: a Institute of Bioorganic Chemistry, Polish Academy of Sciences , Poznan , Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Boryski
mesh_terms: D000215:Acylation; D002254:Carbonates / Q000138:chemical synthesis; D008968:Molecular Conformation; D013816:Thermodynamics; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D002254:Carbonates; D014529:Uridine
keywords: Mitsunobu reaction; calculations; modified nucleosides; nucleoside synthesis; partial acylation