Highly efficient and facile synthesis of 5-azido-2'-deoxyuridine.
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.
Gourdain
Stephanie
S
Universite de Reims Champagne Ardenne, Institut de Chimie Moleculaire de Reims, Reims cedex, France.
Petermann
Christian
C
Harakat
Dominique
D
Clivio
Pascale
P
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
D001386:Azides; D001596:Benzylamines; D019920:Photoaffinity Labels; C030796:benzylamine; D001973:Bromodeoxyuridine; D003857:Deoxyuridine