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

doi:10.1016/j.tet.2004.01.035

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

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2187-2190
Number of pages	4
Journal	Tetrahedron
Volume	60
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2004.01.035
State	Published - Mar 1 2004
Externally published	Yes

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

Access

10.1016/j.tet.2004.01.035

OpenUrl availability

Full text

Fingerprint

Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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. / Bonnac, Laurent; Barragan, Véronique; Winum, Jean Yves et al.
In: Tetrahedron, Vol. 60, No. 10, 01.03.2004, p. 2187-2190.

Research output: Contribution to journal › Article › peer-review

@article{9123ce9aeb1f42698286506c3d13304d,

title = "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",

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.",

keywords = "Alkylsulfamates, Phosphorylation, Pyrophosphate analogues",

author = "Laurent Bonnac and V{\'e}ronique Barragan and Winum, {Jean Yves} and Montero, {Jean Louis}",

note = "Funding Information: Financial support of this work by La Ligue contre le Cancer (Comit{\'e} de l'Aude et du Gard) (L. B PhD fellowship) is gratefully acknowledged.",

year = "2004",

month = mar,

day = "1",

doi = "10.1016/j.tet.2004.01.035",

language = "English (US)",

volume = "60",

pages = "2187--2190",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - New pyrophosphate analogues

T2 - 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

AU - Bonnac, Laurent

AU - Barragan, Véronique

AU - Winum, Jean Yves

AU - Montero, Jean Louis

N1 - 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.

PY - 2004/3/1

Y1 - 2004/3/1

N2 - 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.

AB - 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.

KW - Alkylsulfamates

KW - Phosphorylation

KW - Pyrophosphate analogues

UR - http://www.scopus.com/inward/record.url?scp=1242283839&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1242283839&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.01.035

DO - 10.1016/j.tet.2004.01.035

M3 - Article

AN - SCOPUS:1242283839

SN - 0040-4020

VL - 60

SP - 2187

EP - 2190

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -