(1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters

Journal of Organic Chemistry

Volumn 60, Issue 16, 1995, Pages 5214-5223

  Campagne, Jean Marc ^a   Coste, Jacques ^b   Jouin, Patrick ^b  

^a STANFORD UNIVERSITY   (United States)

^b INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000420816     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00121a045     Document Type: Article

References (62)

1. Nomenclature of Organic Chemistry, Pergamon: Oxford, 1979.
2. Eur. J. Biochem. 1984, 138, 9-37.
3. Castro, B.; Dormoy, J.-R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219-1222.
4. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205-208.
5. Coste, J.; Frérot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
6. Jones, J. The Chemical Synthesis of Peptides; Clarendon: Oxford, 1991; pp 51-55.
7. Castro, B.; Evin, G.; Selve, C.; Seyer, R. Synthesis 1977, 413.
8. Chapleur, Y.; Castro, B.; Toubiana, R. J. Chem. Soc., Perkin Trans. 1 1980, 1940-1943.
9. Itoh, M.; Hagiwara, D.; Notani, J. Synthesis 1975, 456-458.
10. Klausner, Y. S.; Chorev, M. J. Chem. Soc., Chem. Commun. 1975, 973-974.
11. Chorev, M.; Knobler, Y.; Klausner, Y. S. J. Chem. Res., Synop. 1977, 202-203.
12. Dumy, P.; Escale, R.; Vidal, J.-P.; Girard, J.-P.; Parello, J. C. R. Acad. Sci., Ser. II 1991, 312, 235-240.
13. Dumy, P. Ph.D. Dissertation, Université de Montpellier I, Montpellier, France, 1993.
14. Musiol, H.-J.; Grams, F.; Rudolph-Böhner, S.; Moroder, L. J. Org. Chem. 1994, 59, 6144-6146.
15. Campagne, J.-M.; Coste, J.; Jouin, P. Tetrahedron Lett. 1993, 34, 6743-6744.
16. Bartlett, P. A.; Marlowe, C. K. Science 1987, 235, 569-571.
17. Giannousis, P. P.; Bartlett, P. A. J. Med. Chem. 1987, 30, 1603-1609.
18. Bartlett, P. A.; Hanson, J. E.; Giannousis, P. P. J. Org. Chem. 1990, 55, 6268-6274.
19. Hanson, J. E.; Kaplan, A. P.; Bartlett, P. A. Biochemistry 1989, 28, 6294-6305.
20. Pollack, S. J.; Hsiun, P.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 5961-5962.
21. Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069.
22. Sampson, N. S.; Bartlett, P. A. J. Org. Chem. 1988, 53, 4500-4503.
23. Karanewsky, D. S.; Badia, M. C.; Cushman, D. W.; DeForrest, J. M.; Dejneka, T.; Loots, M. J.; Perri, M. G.; Petrillo, E. W., Jr.; Powell, J. R. J. Med. Chem. 1988, 31, 204-212.
24. Malachowski, W. P.; Coward, J. K. J. Org. Chem. 1994, 59, 7625-7634.
25. Morgan, B. P.; Scholtz, J. M.; Ballinger, M. D.; Zipkin, I. D.; Bartlett, P. A. J. Am. Chem. Soc. 1991, 113, 297-307.
26. Campbell, D. A. J. Org. Chem. 1992, 57, 6331-6335.
27. Campbell, D. A.; Bermak, J. C. J. Org. Chem. 1994, 59, 658-660.
28. Campbell, D. A.; Bermak, J. C. J. Am. Chem. Soc. 1994, 116, 6039-6040.
29. Zhao, K.; Landry, D. W. Tetrahedron 1993, 49, 363-368.
30. Tawfik, D. S.; Eshhar, Z.; Bentolila, A.; Green, B. S. Synthesis 1993, 968-972.
31. Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. J. Chem. Soc., Perkin Trans. 1 1984, 2845-2853.
32. Karanewsky, D. S.; Badia, M. C. Tetrahedron Lett. 1986, 27, 1751-1754.
33. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594.
34. Coste, J.; Dufour, M.-N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 31, 669-672.
35. Dourtoglu, V.; Ziegler, J.-C.; Gross, B. Tetrahedron Lett. 1978, 1269-1272.
36. Worms, K. H.; Schmidt-Dunker, M. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1976; Vol. 7, Chapter 18, p 74.
37. Burger, A.; Anderson, J. J. J. Am. Chem. Soc. 1957, 79, 3575-3579.
38. Gold, A. M. J. Org. Chem. 1961, 26, 3991-3994.
39. Dreef, C. E.; Douwes, M.; Elie, C. J. J.; van der Marel, G. A.; van Boom, J. H. Synthesis 1991, 443-447.
40. van der Marel, G.; van Boeckel, C. A. A.; Wille, G.; van Boom, J. H. Tetrahedron Lett. 1981, 22, 3887-3890.
41. Molko, D.; Guy, A.; Téoule, R.; Castro, B.; Dormoy, J.-R. Nouv. J. Chim. 1982, 6, 277-281.
42. Smith, M.; Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1958, 80, 6204-6212.
43. Castro, B.; Dormoy, J.-R. Tetrahedron Lett. 1973, 3243-3246.
44. König, W.; Geiger, R. Chem. Ber. 1970, 103, 788-798.
45. Barlos, K.; Papaioannou, D.; Theodoropoulos, D. Int. J. Pept. Protein Res. 1984, 23, 300-305.
46. Katritzky, A. R.; Malhotra, N.; Fan, W. Q.; Anders, E. J. Chem. Soc., Perkin Trans. 2 1991, 1545-1547.
47. Hudson, R. F.; Keay, L. J. Chem. Soc. 1960, 1859-1864.
48. Kim, M. H.; Patel, D. V. Tetrahedron Lett. 1994, 35, 5603-5606.
49. Abdelmoty, I.; Albericio, F.; Carpino, L. A.; Foxman, B. M.; Kates, S. A. Lett. Pept. Sci. 1994, 1, 57-67.
50. Coste, J.; Castro, B.; Mornon, J. P. Unpublished X-ray data.
51. Ramage, R.; Hopton, D.; Parrot, M. J.; Richardson, R. S.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1985, 461-470.
52. Crofts, P. C. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1973; Vol. 6, pp 51-52.
53. Campagne, J.-M.; Coste, J.; Guillou, L.; Heitz, A.; Jouin, P. Tetrahedron Lett. 1993, 34, 4181-4184.
54. Ottinger, E. A.; Shekels, L. L.; Bernlohr, D. A.; Barany, G. Biochemistry 1993, 32, 4354-4361.
55. Kivinen, A. In The chemistry of acyl halides; Patai, S., Ed.; Interscience: London, 1972; pp 178-222.
56. Horner, L.; Gehring, R. Phosphorus Sulfur 1981, 11, 157-176.
57. Horner, L.; Gehring, R. Phosphorus Sulfur 1982, 12, 295-304.
58. Weidert, P. J.; Geyer, E.; Homer, L. Phosphorus, Sulfur Silicon 1989, 44, 255-259.
59. Horner, L. J. Prakt. Chem. 1992, 334, 645-655.
60. Losse, G.; Bachmann, G. Chem. Ber. 1964, 97, 2671-2680.
61. Losse, G.; Klengel, H. Tetrahedron 1971, 27, 1423-1434.
62. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119-144.