Efficient synthesis of nucleoside aryloxy phosphoramidate prodrugs utilizing benzyloxycarbonyl protection

An efficient method for the synthesis of nucleoside phosphoramidates prodrugs ( 6a– f) has been developed that employs a simple protection/deprotection sequence of the nucleoside with benzyloxycarbonyl (Cbz). The coupling reaction of Cbz-protected derivatives ( 5a– f) with phenyl-(ethoxy- l-alaninyl...

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Veröffentlicht in:	Tetrahedron 2011-07, Vol.67 (30), p.5487-5493
Hauptverfasser:	Cho, Jong Hyun, Amblard, Franck, Coats, Steven J., Schinazi, Raymond F.
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral Antiviral agents Benzyloxycarbonyl Biological and medical sciences Carbohydrates. Nucleosides and nucleotides Chemical compounds Chemical reactions Chemistry Derivatives Drugs Exact sciences and technology Hydrogenolysis Medical sciences Monophosphate prodrug Nucleoside Nucleosides Nucleosides, nucleotides and oligonucleotides Organic chemistry Pharmacology. Drug treatments Preparations and properties ProTide Synthesis (chemistry) Tetrahedrons
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Beschreibung
Zusammenfassung:	An efficient method for the synthesis of nucleoside phosphoramidates prodrugs ( 6a– f) has been developed that employs a simple protection/deprotection sequence of the nucleoside with benzyloxycarbonyl (Cbz). The coupling reaction of Cbz-protected derivatives ( 5a– f) with phenyl-(ethoxy- l-alaninyl)-phosphorochloridate ( 7), followed by Cbz group removal by hydrogenolysis provided the phenyl phosphoramidate ProTides ( 6a– f) in excellent overall yields. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2011.05.046