Synthesis of (R)- and (S)-ßhydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside ß-ketophosphonate, readly available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-ß-hydroxyphosphonate derivatives which was resolved....
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Veröffentlicht in: | Tetrahedron: asymmetry 2011, Vol.22, p.1505-1511 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside ß-ketophosphonate, readly available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-ß-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. |
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ISSN: | 0957-4166 0957-4166 |
DOI: | 10.1016/j.tetasy.2011.08.010 |