Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

Nicholas Powles, John Atherton, Michael I. Page

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5940-5947
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number30
DOIs
Publication statusPublished - 14 Aug 2012

Fingerprint Dive into the research topics of 'Reactive intermediates in the H-phosphonate synthesis of oligonucleotides'. Together they form a unique fingerprint.

  • Cite this