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

Tetrahedron

Volumn 60, Issue 10, 2004, Pages 2187-2190

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

^a INSTITUT CHARLES GERHARDT   (France)

Author keywords

Alkylsulfamates; Phosphorylation; Pyrophosphate analogues

Indexed keywords

ALKENE DERIVATIVE; BROMOTRIMETHYLSILANE; N (O DODECYLSULFAMOYL)PHOSPHORAMIDIC ACID; N (O HEXADECYLSULFAMOYL)PHOSPHORAMIDIC ACID; N (O OCTYLSULFAMOYL)PHOSPHORAMIDIC ACID; N (O SULFAMOYL)PHOSPHORAMIDIC ACID; N (O SULFAMOYL)TRIMETHYLPHOSPHA LAMBDA 5 AZENE; N (O TETRADECYLSULFAMOYL)PHOSPHORAMIDIC ACID; PHOSPHORAMIDIC ACID DERIVATIVE; PYROPHOSPHORIC ACID DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; HYDROLYSIS; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

EID: 1242283839     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.035     Document Type: Article

References (19)

1. Jennings L.J., Macchia M., Parkin A. J. Chem. Soc., Perkin Trans. 1. 1992;2197-2202.
2. Schaeffer M.J., Beauchamp L., De Miranda P., Elion G.B., Bauer D.J., Collins P. Nature. 272:1978;583-585.
3. De Clercq E., Holy A., Rosenberg I., Sakuma T., Balzarini J., Mandgal P.C. Nature. 323:1986;464-467.
4. De Clercq E., Sakuma T., Baba M., Pauwels R., Balzarini J., Rosenberg I., Holy A. Antiviral Res. 8:1987;261-272.
5. Huryn D.M., Okabe M. Chem. Rev. 92:1992;1745-1768.
6. Saady M., Lebeau L., Miokowski C. Tetrahedron Lett. 36:1995;4237-4240.
7. Tanaka Y., Morita C.T., Tanaka Y., Nieves E., Brenner M.B., Bloom B.R. Nature. 375:1995;155-158.
8. Tanaka Y., Brenner M.B., Bloom B.R., Morita C.T. J. Mol. Med. 74:1996;223-231.
9. Morita C.T., Tanaka Y., Bloom B.R., Brenner M.B. Forum Immunol. 1996;347-353.
10. Boudjabi B., Dewynter G., Montero J.-L. Synlett. 5:2000;716-718.
11. Macchia M., Martinelli A., Parkin A., Rosselo A. Il Farmaco. 49:1994;325-332.
12. Okada M., Iwashita S., Koizumi N. Tetrahedron Lett. 41:2000;7047-7051.
13. Winum J.-Y., Vullo D., Casini A., Montero J.-L., Scozzafava A., Supuran C.T. J. Med. Chem. 46:2003;2197-2204.
14. Schwesinger R., Willaredt J., Schlemper H., Keller M., Schmitt D., Fritz H. Chem. Ber. 127:1994;2435-2454.
15. Yoshikawa M., Kato T., Takenishi T. Tetrahedron Lett. 50:1967;5065-5068.
16. Levchenko E.S., Sheinkman I.E., Kirsanov A.V. Zh. Obshch. Khim. 30:1960;1941-1946. [Chem. Abstr. 55, 6426a].
17. Zhu S., Xu G., Qin C., Xu Y., Chu Q. Phosphorus, Sulfur Silicon. 140:1998;53-61.
18. McKenna C.E., Higa M.T., Cheung N.H., McKenna M.C. Tetrahedron Lett. 2:1977;155-158.
19. Marsmann, H. NMR spectroscopy; Basic Principles and Progress; Vol. 17, Diehl, E., Fluck, E. & Kosfeld, R., Eds., Springer-Verlag, Berlin, 1981, p. 65.