New pyrophosphate analogues: A facile access to N-(O-alkyl-sulfamoyl) phosphoramidic acids via a simple and quantitative reaction of N-(O-alkylsulfamoyl)trimethylphospha-λ5-azene with bromotrimethylsilane and water

Laurent Bonnac, Véronique Barragan, Jean Yves Winum, Jean Louis Montero

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3 Scopus citations

Abstract

A new strategy to prepare pyrophosphate analogues through selective and quantitative cleavage of N-(O-alkylsulfamoyl)trialkylphospha-λ 5-azene esters (R-O-SO2-NP(OR′)3) has been developed. Using pure bromotrimethylsilane, N-(O-alkyl-sulfamoyl) tristrimethylsilylphospha-λ5-azenes (R-O-SO 2-NP(OSiMe3)3) have been easily obtained as intermediates. N-(O-Alkyl-sulfamoyl)phosphoramidic acids (R-O-SO 2-NH-P(O)(OH)2) have been formed quantitatively by hydrolysis of the silylated intermediates.

Original languageEnglish (US)
Pages (from-to)2187-2190
Number of pages4
JournalTetrahedron
Volume60
Issue number10
DOIs
StatePublished - Mar 1 2004
Externally publishedYes

Bibliographical note

Funding Information:
Financial support of this work by La Ligue contre le Cancer (Comité de l'Aude et du Gard) (L. B PhD fellowship) is gratefully acknowledged.

Keywords

  • Alkylsulfamates
  • Phosphorylation
  • Pyrophosphate analogues

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