2,4-dinitrophenol as an activating reagent in a facile preparation of cyclic phosphate trimesters

Marie Migaud, Eric Amigues

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Abstract 2,4-Dinitrophenol was employed with benzyloxy-bis-(diisopropylamino)phosphine to synthesise the cyclic phosphate derivatives of a series of alkane diols (HO–(CH2)n–OH, n=2–6) in good isolated yields. Tetrazole and DNP were compared by 31P NMR spectroscopy for their ability to catalyse the cyclisation at the P(III) stage. Investigation of the phosphate triester stability under various oxidation and chromatographic conditions resulted in the optimisation of the isolation procedures of the chemically unstable cyclic compounds. Conditions for debenzylation were developed to yield the corresponding cyclic phosphodiesters quantitatively. The methodology was further applied to the preparation and isolation of the cyclic phosphate derivative of a carbohydrate.
Original languageEnglish
Pages (from-to)1001-1004
Number of pages4
JournalTetrahedron Letters
Volume45(5)
Issue number5
DOIs
Publication statusPublished - 26 Jan 2004

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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