title: Highly efficient and facile synthesis of 5-azido-2'-deoxyuridine.
abstract: Previously reported syntheses of the photoaffinity label 5-azido-2'-deoxyuridine are rather inefficient and involve the tedious preparation of a 5-nitro intermediate. To overcome these inconveniences, we have developed a new approach from the commercially available 5-bromo-2'-deoxyuridine nucleoside. Our synthetic route makes use of a benzylamination reduction sequence. Using this strategy, the 5-azido-2'-deoxyuridine photolabel is prepared in three steps and quantitative yields.
authors.affiliation: Universite de Reims Champagne Ardenne, Institut de Chimie Moleculaire de Reims, Reims cedex, France.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Gourdain
authors.forename: Christian
authors.initials: C
authors.lastname: Petermann
authors.forename: Dominique
authors.initials: D
authors.lastname: Harakat
authors.forename: Pascale
authors.initials: P
authors.lastname: Clivio
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry; D001973:Bromodeoxyuridine / Q000737:chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001386:Azides; D001596:Benzylamines; D019920:Photoaffinity Labels; C030796:benzylamine; D001973:Bromodeoxyuridine; D003857:Deoxyuridine