Difluoromethylenediphosphonate: A convenient, scalable, and high-yielding synthesis

Organic Letters

Volumn 8, Issue 2, 2006, Pages 187-189

  Boyle, Nicholas A ^a,b  

^a Biota Inc   (United States)

^b Pacific Life Sciences Consulting   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31644450345     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0522889     Document Type: Article

References (49)

1. (a) Boyle, N. A.; Fagan, P.; Brooks, J. L.; Prhavc, M.; Lambert, J.; Cook, P. D. Nucleosides Nucleotides Nucleic Acids 2005, 24, in press.
2. (b) Rajwanshi, V. K.; Prhavc, M.; Fagan, P.; Brooks, J. L.; Hurd, T, Cook, P. D.; Wang, G. Nucleosides Nucleotides Nucleic Acids 2005, 24 (3), 179-189.
3. (c) Boyle, N. A.; Rajwanshi, V.; Prhavc, M.; Wang, G.; Fagan, P.; Chen, F.; Ewing, G.; Brooks, J. L.; Hurd, T.; Bruice, T, W.; Cook, P. D. Synthesis of Dideoxynucleoside. J. Med. Chem. 2005, 48 (7), 2695-2700.
4. (d) Wang, G.; Boyle, N. A.; Chen, F.; Rajappan, V.; Fagan, P.; Brooks, J. L.; Hurd, T.; Leeds, J. M.; Bruice, T. W.; Rajwanshi, V.; Jin, Y.; Prhavc, M.; Cook, P. D. J. Med. Chem. 2004, 47 (27), 6902-6913.
5. (e) Wang, G.; Sakhivel, K.; Rajappan, V.; Bruice, T. W.; Tucker, K.; Fagan, P.; Brooks, J. L.; Hurd, T.; Leeds, J. M.; Cook, R. D. Nucleosides Nucleotides Nucleic Acids 2004, 23 (1-2), 317-337.
6. (f) Cook, P. D.; Ewing, G.; Jin, Y.; Lambert, J.; Prhavc, M.; Rajappan, V.; Rajwanshi, V. K.; Sakthivel, K. PCT Int. Appl. WO2005021568, 2005.
7. Proctor & Gamble. GB1026366, April 20, 1966. This and other patents available free of charge from the European Patent Office: http:// ep.espacenet.com/search97cgi/s97_cgi.exe?Action=FormGen&Template=ep/EN/home. hts.
8. (a) Blackburn, G. M.; England, D. A.; Kolkmann, F. Monofluoro- and Difluoro-methylenebisphosphonic Acids: Isopolar Analogues of Pyrophosphoric Acid. J. Chem. Soc., Chem. Commun. 1981, 17, 930-932.
9. (b) Also see: Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58 (8), 2272-2281.
10. For example: (a) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 22, 1188-1190.
11. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 5, 1119-1125.
12. (c) Blackburn, G. M.; Perree, T. D.; Rashid, A.; Bisbal, C.; Lebleu, B. Chem. Scr. 1986, 26 (1), 21-24.
13. For example: (a) Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 51 (25), 4768-4779.
14. (b) Stremler, K. E. and Poulter, C. D. J. Am. Chem. Soc. 1987, 109 (18), 5542-5544.
15. For example: (a) Davisson, V. J.; Davis, D. R.; Dixit, V. M.; Poulter, C. D. J. Org. Chem. 1987, 52, 2 (9), 1794-1801.
16. (b) Ariza, M. E.; Leeds, J. M.; Williams, M. V.; Boyle, N. A.; Wang, G.; Prhavc, M.; Rajwanshi, V.; Chen, F.; Brooks, J.; Hurd, T.; Cook, P. D. Poster presentation at the 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Chicago, IL, Sep 2003.
17. For example: Rowe, D. J.; Hays, S. J. Metab. Bone Dis. Relat. 1983, 5 (1), 13-16.
18. For example: Mahmood, T.; Shreeve, J. M. Inorg. Chem. 1986, 25, 3128-3131.
19. Selected recent examples: (a) Spelta, V.; Mekhalfia, A.; Rejman, D.; Thompson, M.; Blackburn, G. M.; North, A. R. Brit. J. Pharmacol. 2003, 140 (6), 1027-1034.
20. (b) White, P. J.; Webb, T. E.; Boarder, M. R. Mol. Pharmacol. 2003, 63 (6), 1356-1363.
21. (c) Klein, E.; Nghiem, H.-O.; Valleix, A.; Mioskowski, C.; Lebeau, L. Chem.-Eur. J. 2002, 8 (20), 4649-4655.
22. (d) Simon, J.; Filippov, A. K.; Goransson, S.; Wong, Y. H.; Frelin, C.; Michel, A. D.; Brown, D. A.; Barnard, E. A. J. Biol. Chem. 2002, 277 (35), 31390-31400.
23. (e) Khandazhinskaya, A. L.; Shirokova, E. A.; Skoblov, Y. S.; Victorova, L. S.; Goryunova, L. Y.; Beabealashvilli, R. S.; Pronyaeva, T. R.; Fedyuk, N. V.; Zolin, V. V.; Pokrovsky, A. G.; Kukhanova, M. K. J. Med. Chem. 2002, 45 (6), 1284-1291.
24. (f) Pankiewicz, K. W.; Lesiak-Watanabe, K. B.; Watanabe, K. A.; Patterson, S. E.; Jayaram, H. N.; Yalowitz, J. A.; Miller, M. D.; Seidman, M.; Majumdar, A.; Prehna, G.; Goldstein, B. M. J. Med. Chem. 2002, 45 (3), 703-712.
25. (g) Wine, D. W.; Ohlsen, L. J. U.S. Pat. Appl. Publ. 2005. US2005084737.
26. (h) Lovdahl, M. J.; Pietrzyk, D. J. J. Chromatog. A 1999, 850 (1+2), 143-152.
27. (i) See ref 1.
28. (a) Burton, D. J.; Flynn, R. M. J. Fluorine Chem. 1980, 15, 263-266.
29. (b) Blackburn, G. M.; England, D. A.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 17, 930-932.
30. (c) Bystrom, C. E.; Pettigrew, D. W.; Remington, S. J.; Branchaud, B. P. Bioorg. Med. Chem. Lett. 1997, 7 (20), 2613-2616. A specific yield was not given.
31. (d) Hutchinson, D. W.; Thornton, D. M. J. Organomet. Chem. 1988, 340, 93-99.
32. (e) Blackburn, G. M.; Taylor, G. E. J. Organomet. Chem. 1988, 348, 55-61.
33. (f) Chambers, R. D.; Hutchinson, J. J. Fluorine Chem. 1998, 92, 45-52.
34. (g) Obayashi, M.; Ito, E.; Matsui, K.; Kondo, K. Tetrahedron Lett. 1982, 23 (22), 2323-2326.
35. (h) Hamilton, C. J.; Roberts, S. M.; Shipitsin, A. Chem. Commun. 1998, 1087-1088.
36. (i) Shipitsin, A. V.; Victorova, L. S.; Shirokova, E. A.; Dyatkina, N. B.; Goryunova, L. E.; Beabealashvilli, R. S.; Hamilton, C. J.; Roberts, S. M.; Krayevsky, A. J. Chem. Soc., Perkin Trans. 1 1999, 1039-1050.
37. (j) Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186.
38. (k) Nair, H. K.; Burton, D. J. Tetrahedron Lett. 1995, 36 (3), 347-350.
39. (l) McKenna, C. E.; Shen, P. J. Org. Chem. 1981, 46, 4573-4576.
40. (m) Hebel, D.; Kirk, K. L.; Kinjo, J.; Kovács, T.; Lesiak, K.; Balzarini, J.; De Clercq, E.; Torrence, P. F. Bioorg. Med. Chem. Lett. 1991, 1 (7), 357-360.
41. Laux, W. H. G.; Périgaud, C.; Imbach, J.-L.; Gosselin, G. Nucleosides Nucleotides 1999, 18 (4-5), 1003-1004.
42. Blackburn, G. M.; Thompson, M. Personal communication.
43. Cook, P. D.; Wang, G.; Bruice, T. W.; Boyle, N. A.; Leeds, J. M.; Brooks, J. L.; Prhavc, M.; Ariza, M. E.; Fagan, P. C.; Jin, Y.; Rajwanshi, V. K.; Tucker, K. D. Biota, Inc., USA. PCT Int. Appl. WO2003072757, 2003.
44. (a) Kudo, S. Konica Corp., Japan. U.S. Pat. Appl. Publ. US2004-005521, 2005.
45. (b) See ref 8g.
46. For examples, see: (a) Hamilton, C. J.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 8, 1051-1056.
47. (b) Grison, C.; Coutrot, P.; Comoy, C.; Balas, L.; Joliez, S.; Lavecchia, G.; Oliger, P.; Penverne, B.; Serre, V.; Herve, G. Eur. J. Med. Chem. 2004, 39 (4), 333-344.
48. (a) Boyle, N. A.; Chegwidden, W. R.; Blackburn, G. M. Org. Biomol. Chem. 2005, 3 (2), 222-224.
49. (b) Blackburn, G. M. and Tuerkmen, H. Org. Biomol. Chem. 2005, 3 (2), 225-226.