Highly efficient and facile synthesis of 5-azido-2'-deoxyuridine.

Nucleosides, nucleotides & nucleic acids (2010-07-01)
Stephanie Gourdain, Christian Petermann, Dominique Harakat, Pascale Clivio
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Sigma-Aldrich
Benzylamine hydrochloride
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%