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Synlett 1998; 1998(3): 283-285
DOI: 10.1055/s-1998-1632
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The Utilization of Secondary Phosphine Oxide Synthons for the Preparation of Novel Tertiary Phosphine Oxide Modified DNA

Stephen P. Collingwood* , Roger J. Taylor
  • *Novartis Pharmaceuticals Central Research, Hulley Road, Macclesfield, Cheshire, SK10 2NX, U.K.
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Publication History

Publication Date:
31 December 2000 (online)

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Novel tertiary phosphine oxides are described which act as masked secondary phosphine oxides. The protection of the reactive P-H bond allows generation of a carbanion alpha to phosphorus and subsequent alkylation with an oxetane. The free P-H can then be liberated with anhydrous acid. This functionality can then be further alkylated to generate novel tertiary phosphine oxide backbone modified DNA.

antisense - nucleic acid - phosphine oxide - nucleotide analogue

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