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Synlett 2001; 2001(4): 0473-0476
DOI: 10.1055/s-2001-12329
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Stereochemical Assignment and Stereoselective Synthesis of 3′-C-P-N-5′ R P-Ethyl Phosphonamidate Modified Nucleic Acid

Robin A. Fairhurst* , Stephen P. Collingwood, David Lambert
  • *Novartis Pharmaceuticals, Central Research Laboratories, Hulley Road, Macclesfield, Cheshire, SK10 2NX, UK; Fax + 44 (0) 1403 323307; E-mail: robin.fairhurst@pharma.novartis.com
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Publication History

Publication Date:
31 December 2001 (online)

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The configuration of the duplex stabilising 3′-C-P-N-5′ ethyl phosphonamidate nucleic acid backbone modification has been identified as R P following the preparation of cyclic nucleoside analogues and NOF studies. Complimentary routes for formation of the key phosphonamidate nitrogen to phosphorus bond from stereochemically defined H-phosphinate intermediates, involving both a retention and inversion at the phosphours centre, have been identified.

antisense - modified oligonucleotides - phosphorus protecting groups - stereoselective