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Issue 30, 2012
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Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

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Abstract

The formation of H-phosphonate diesters is an important step in the synthesis of oligonucleotides. Using diphenylchlorophosphate as the activator for the coupling step is often accompanied by side reactions as a result of self ‘capping’ and other reactions of the reactive intermediate. In the absence of base, the activation of ethyl H-phosphonate with diphenylchlorophosphate probably occurs through the intermediate formation of bis diethyl pyro-di-H-phosphonate rather than the expected diphenyl ethyl pyro-H-phosphonate. Pyridine acts as a nucleophilic catalyst converting diphenylchlorophosphate to its pyridinium adduct. Several side and unwanted reactions are quantified so that conditions to minimise these can be identified.

Graphical abstract: Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

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Publication details

The article was received on 19 Dec 2011, accepted on 24 Apr 2012 and first published on 07 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB07130D
Citation: Org. Biomol. Chem., 2012,10, 5940-5947
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    Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

    N. Powles, J. Atherton and M. I. Page, Org. Biomol. Chem., 2012, 10, 5940
    DOI: 10.1039/C2OB07130D

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