2022
DOI: 10.1021/acs.joc.2c01582
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Synthesis of Phosphorodiamidate Oligonucleotide Dimers

Abstract: Azido nucleosides couple with phosphoramidites via an initial iminophosphorane, which eliminates acrylonitrile to generate the coupled dimer P­(V) product. The vulnerable phosphite triester intermediate is bypassed entirely, making the methodology very suitable to solution-phase synthesis. This new coupling protocol requires no protection of the 5′-OH function and provides a new method of installing internucleosidic phosphorodiamidate bonds with near quantitative yields.

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