Synthesis of new acyclic nucleoside phosphonates (ANPs) substituted on the 1&; prime; and/or 2&; prime; positions

Synthesis of new acyclic nucleoside phosphonates (ANPs) substituted on the 1&; prime; and/or 2&; prime; positions

A series of 2\' functionalized acyclic nucleoside phosphonate derivatives of 1-[3\'-(phosphonomethoxy)propyl]uracil (1-4) have been synthesized together with the 1\' and 2\'-ethynyl derivatives of 9/1-[2\'-(phosphonomethoxy)ethyl]adenine/thymine (5-7). Key intermediates lead...

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Veröffentlicht in:Tetrahedron letters 2011-12, Vol.52 (51), p.6896-6898
Hauptverfasser: Kundarapu, Maheshwar, Marchand, Damien, Dumbre, Shrinivas G, Herdewijn, Piet
Format: Artikel
Sprache:eng
Schlagworte:
Derivatives
Nucleosides
Phosphonates
Synthesis (chemistry)
Tetrahedrons
Thymine
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Zusammenfassung:A series of 2\' functionalized acyclic nucleoside phosphonate derivatives of 1-[3\'-(phosphonomethoxy)propyl]uracil (1-4) have been synthesized together with the 1\' and 2\'-ethynyl derivatives of 9/1-[2\'-(phosphonomethoxy)ethyl]adenine/thymine (5-7). Key intermediates leading to the latter series are (+/-)-[2-{diethyl(phosphonomethoxy)}-1-hydroxy]-but-3-yne (25) and (+/-)-diisopropyl{[2-hydroxy-4-(trimethylsilyl)but-3-yn-1-yl]o xy}methylphosphonate (30). Compounds 25 and 30 are easily obtained starting from (+/-)-solketal.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.10.037