Highly efficient and facile synthesis of 5-azido-2'-deoxyuridine
Stephanie Gourdain1, Christian Petermann, Dominique Harakat
1Universite de Reims Champagne Ardenne, Institut de Chimie Moleculaire de Reims, Reims cedex, France.
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.
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