A combinatorial method for the solid phase synthesis of α-amino phosphonates and phosphonic acids

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5457-5460

  Zhang, Chengzhi ^a   Mjalli, Adnan M M ^a  

^a Ontogen Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; PHOSPHONOAMINO ACID;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030605892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01193-8     Document Type: Article

References (28)

1. 1. Thompson, L, A.; Ellman, J. A. Chem. Rev. 1996, 96, 555, and references therein.
2. 2. For examples of radio frequency encoded libraries see: (a) Mjalli, A. M. M.; Toyonaga, B. E. Net. Sci. 1995, 1, http://www.awod.com/netsci.
3. (b) Moran, E. J.; Sarshar, S.; Cargill, J. F.; Shabaz; M.; Lio, A.; Mjalli, A. M. M.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 10787.
4. (c) Nicolaou, K. C.; Xiao, Y.; Parandoosh, Z.; Senyei, A.; Nove, M. P. Angew. Chem. 1995, 107, 2476.
5. 3. For examples of spatially dispersed libraries see: (a) Armstrong, R. W. WO 95192566, 1995.
6. (b) Hobbs Dewitt, S.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. USA 1993, 90, 6909.
7. 4. (a) Sarshar, S.; Siev, D.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 835.
8. (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751.
9. (c) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
10. (d) Steele, J.; Gordon, D. W. Bioorg. & Med. Chem. Lett 1995, 5, 47.
11. (e) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
12. 5. (a) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
13. (b) EPSP synthase: Sikorski, J. A. et. al. Phosphorus, Sulfur and Silicon 1993, 76, 115.
14. (c) HIV protease: Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1989, 33, 6625.
15. (d) PTPases: Burke, T. R., Jr.; Barchi, J. J., Jr.; George, C.; Wolf, G.; Shoelson, S. E.; Yan, X. J. Med. Chem. 1995, 38, 1386.
16. 6. Wang, S. S. J. Am. Chem. Soc. 1973, 95, 1328.
17. 7. (a) Cao, X.; Mjalli, A. M. M. Tetrahedron Lett. 1996, submitted.
18. Polymers 2 and 3 are stable for up to 6 months at 23°C when kept in a vacuum dessicator, (b) Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1986, 27, 469.
19. (c) Marugg, J. E. Tromp, M.; Kuyl-Yeheskiely, E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 2661.
20. 1 H NMR using an internal standard (Methyl 4-bromobenzoate).
21. 9. Blazis, V. J.; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931.
22. 10. (a) Yager, K. M.; Taylor C. M.; Smith, III, A. B. J. Am. Chem. Soc. 1994, 116, 9377.
23. (b) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467.
24. 11 Solutions of imines were prepared by incubating the aldehyde and the amine in the indicated solvent overnight at 23°C in the presence of 4 Å molecular sieves (activated at 100°C).
25. 3 catalysed addition of silyl enol ethers to imines see: Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
26. 13. Hubert, C.; Munoz, A. J. Org. Chem. 1995, 60, 1488.
27. 4PN [M-H] : 362.
28. 15. Himmelsbach, F.; Schultz, B. S.; Trichtinger, T.; Charubala, R.;Pfleiderer, W. Tetrahedron Lett. 1984, 40, 59.