Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides
Practical and convergent syntheses of 2‘-deoxy-1‘,2‘-seco-nucleophosphonates and 1‘,2‘-seco-nucleophosphonates are described. Phosphonate chirons derived from d-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequen...
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| Veröffentlicht in: | Journal of organic chemistry 1996-02, Vol.61 (3), p.890-894 |
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| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | Practical and convergent syntheses of 2‘-deoxy-1‘,2‘-seco-nucleophosphonates and 1‘,2‘-seco-nucleophosphonates are described. Phosphonate chirons derived from d-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5‘-C-methylenephosphonic acids which were conveniently purified using gravity flow C18 reverse phase column chromatography. |
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| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo951701v |