A solid supported synthesis of thiol esters

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4305-4308

  Adamczyk, Maciej ^a   Fishpaugh, Jeffrey R ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 DIMETHYLAMINOPROPYL) 3 ETHYLCARBODIIMIDE; CARBOXYLIC ACID; POLYMER; THIOESTER; THIOL;

ARTICLE; CHEMICAL REACTION; CONJUGATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SOLID; STEREOSPECIFICITY; SYNTHESIS;

EID: 0029949395     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00831-3     Document Type: Article

References (36)

1. a) Halcomb, R. et al. J. Am. Chem. Soc. 1995, 117, 5720.
2. b) Corey, E. and Reichard, G. J. Am. Chem. Soc. 1992, 114, 10677.
3. Stryer, L. in Biochemistry, W.H. Freeman and Co., New York, 1988, chapter 20.
4. Bolasco, F. U.S. Patent No. 4, 242, 354, 1980.
5. Field, L. Synthesis 1972, 101 and references therein.
6. McGarvey, G. et al. J. Am. Chem. Soc. 1986, 108, 4943.
7. Conrow, R. and Portoghese, P. J. Org. Chem. 1986, 51, 938.
8. Kawanami, Y.; Katsuki, T. and Yamaguchi M. Tetrahedron Lett. 1983, 24, 5131.
9. Nagao, Y.; Kawabata, K. and Fujita E. J.Chem Soc. Chem. Commun., 1978, 330.
10. Penn J. and Owens W. Tetrahedron Lett. 1992, 33, 3737.
11. Fukuyama, T.; Lin, S. and Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
12. Liu, H.; Bukownik, R. and Pednekar, P. Syn. Comm. 1981, 11, 599.
13. Liu, H. and Luo, W. Syn. Comm. 1989, 19, 387.
14. Masamune, S.; Bates, G. and Corcoran, J. Angew. Chem. Int. Ed. Engl. 1977, 16, 585.
15. Mohanraj, S. and Ford, W. J. Org. Chem. 1985, 50, 1616.
16. Baca, M.; Muir, T.; Schnolzer, M. and Kent, S. J. Am. Chem. Soc. 1995, 117, 1881 and references therein.
17. Frykman, H.; Ohrner, N.; Norin, T. and Hult, K. Tetrahedron Lett. 1993, 34, 1367, see also Fang, J. and Wong, C. Synlett 1994, 393 for other uses of thiol esters in enzymatic reactions.
18. Frykman, H.; Ohrner, N.; Norin, T. and Hult, K. Tetrahedron Lett. 1993, 34, 1367, see also Fang, J. and Wong, C. Synlett 1994, 393 for other uses of thiol esters in enzymatic reactions.
19. Benz, H. Synthesis 1994, 337.
20. Alpegiani, M. et al Eur. J. Med. Chem. 1992, 27, 875.
21. Annunziata, R.; Benaglia, M.; Cinquini, M. and Cozzi, F. Tetrahedron Lett. 1995, 36, 613.
22. Davis, A. and Walsh, J. Tetrahedron Lett. 1994, 35, 4865.
23. Suh, K. and Choo, D. Tetrahedron Lett. 1995, 36, 6109.
24. a) Imamoto, T.; Kodera, M. and Yokoyama, M. Synthesis 1982, 134 (Polyphosphate ester).
25. b) Liu, H. and Sabesan, S. Can. J. Chem. 1980, 58, 2645 (Phenyl dichlorophosphate).
26. c) Grunwell, J. and Forest, D. Synth. Commun. 1976, 6, 453 (Dicyclohexylcarbodiimide).
27. d) Saegusa, Y.; Watanabe, T. and Nakamura, S. Bull. Chem. Soc. Jpn. 1989, 62, 539.
28. e) Kim, M. and Patel, D. Tetrahedron Lett. 1994, 35, 5603 (BOP).
29. Spessard, G.; Chan, W. and Masamune, S. Org Synth. 1982, 61, 134.
30. Ahmad, S. and Iqbal, J. Tetrahedron Lett. 1986, 27, 3791.
31. Endo, T.; Ikenaga, S. and Mukaiyama, T. Bull. Chem. Soc. Jpn. 1970, 43, 2633.
32. Petrillo, G.; Novi, M.; Garbarino, G. and Filiberti, M. Tetrahedron 1989, 45, 7411.
33. Sucheta, K.; Reddy, G.; Ravi, D. and Rao, N. Tetrahedron Lett. 1994, 35, 4415.
34. Some advantages of solid support are simple isolation, good reproducibility of product and amenable to automation as exemplified by peptide synthesis using Merrifield's methodology.
35. Adamczyk, M.; Fishpaugh, J. and Mattingly, P. Tetrahedron Lett. 1995, 36, 8345.
36. Desai, M. and Stramiello, L. Tetrahedron Lett. 1993, 34, 7685.