A synthesis of bredinin (Mizoribine®) from an acyclic precursor

Bredinin (4-carbamoyl-1-β- d-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate from 2,3-isopropylidene- d-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotect...

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Veröffentlicht in:	Tetrahedron letters 2011-11, Vol.52 (47), p.6223-6227
Hauptverfasser:	Humble, Robert W., Middleton, Danielle F., Banoub, Joseph, Ewing, David F., Boa, Andrew N., Mackenzie, Grahame
Format:	Artikel
Sprache:	eng
Schlagworte:	5-Hydroxyimidazole Carbohydrates. Nucleosides and nucleotides Chemistry Chlorides Cyclisation Exact sciences and technology Formations Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Nucleoside Nucleosides, nucleotides and oligonucleotides Organic chemistry Oximes Precursors Preparations and properties Reduction Synthesis (chemistry) Tetrahedrons
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Beschreibung
Zusammenfassung:	Bredinin (4-carbamoyl-1-β- d-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate from 2,3-isopropylidene- d-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.09.085