New efficient synthesis of 1-hydroxymethylene-1,1-bisphosphonate monomethyl esters

Synlett

Volumn , Issue 3, 2005, Pages 425-428

  Migianu, Evelyne ^a   Guénin, Erwann ^a   Lecouvey, Marc ^a  

^a UNIVERSITÉ PARIS 13   (France)

Author keywords

ketophosphonates; 1 hydroxymethylene 1,1 bisphosphonates; Arbuzov reaction; Bis(silylated) phosphite

Indexed keywords

ACID; BISPHOSPHONIC ACID DERIVATIVE; CARBENOID; CHLORIDE; ESTER DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SILYLATION; STEREOISOMERISM;

EID: 14644393585     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837226     Document Type: Article

References (24)

1. Page, P. C. B.; McKenzie, M. J.; Gallagher, J. A. J. Org. Chem. 2001, 66, 3704.
2. Page, P. C. B.; McKenzie, M. J.; Gallagher, J. A. Synth. Commun. 2002, 32, 211.
3. Vovk, A. I.; Kalchenko, V. I.; Cherenok, S. A.; Kukhar, V. P.; Muzychka, O. V.; Lozynsky, M. O. Org. Biomol. Chem. 2004, 2, 3162.
4. Fleisch, H. Endocr. Rev. 1998, 19, 80.
5. Fleisch, H. Prog. Mol. Subcell. Biol 1999, 23, 197.
6. Fleisch, H. Eur. Spine J. 2003, 12 Suppl. 2, S142.
7. Green, J. R. Cancer 2003, 97, 840.
8. Mercadante, S. Curr. Urol. Rep. 2002, 3, 244.
9. Clezardin, P.; Fournier, P.; Boissier, S.; Peyruchaud, O. Curr. Med. Chem. 2003, 10, 173.
10. Fleisch, H. Breast Cancer Res. 2002, 4, 30.
11. Lin, J. H. Bone 1996, 18, 75.
12. Niemi, R,; Turbanen, P.; Vepsalainen, J.; Taipale, H.; Jarvinen, T. Eur. J. Pharm. Sci. 2000, 11, 173.
13. Vepsalainen, J. J. Curr. Med. Chem. 2002, 9, 1201.
14. Ezra, A.; Hoffman, A.; Breuer, E.; Alferiev, I. S.; Monkkonen, J.; El Hanany-Rozen, N.; Weiss, G.; Stepensky, D.; Gati, I.; Cohen, H.; Tormalehto, S.; Amidon, G. L.; Golomb, G. J. Med. Chem. 2000, 43, 3641.
15. Fitch, S. J.; Moedritzer, K. J. Am. Chem. Soc. 1962, 84, 1876.
16. Turhanen, P. A.; Ahlgren, M. J.; Jaervinen, T.; Vepsaelaeinen, J. J. Synthesis 2001, 633.
17. Migianu, E.; Mallard, I.; Bouchemal, N.; Lecouvey, M. Tetrahedron Lett. 2004, 45, 4511.
18. Mallard, I. Ph.D. Thesis; Université: Paris 13, 2002.
19. El Manouni,D.; Leroux, Y.; Burgada, R. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 42, 73.
20. Sekine, M.; Futatsugi, T.; Yamada, K.; Hata, T. J. Chem. Soc., Perkin Trans, 1 1982, 11, 2509.
21. Lecouvey, M.; Leroux, Y.; Kraemer, M.; Crepin, M.; El Manouni, D.; Louriki, M. PCT Int. Appl. WO 03008425, 2003; Chem. Abstr. 2003, 138, 122736.
22. Migianu, E.; Monteil, M.; Even, P.; Lecouvey, M. Nucleosides, Nucleotides Nucleic Acids 2004, accepted.
23. 4P: C, 50.48; H, 5.18; P, 14.46. Found: C, 50.39; H, 5.20; P, 14.51.
24. 2: C, 34.06; H, 4.29; P, 21.96. Found: C, 34.21; H, 4.32; P, 21.91.