Development of new linkers for the formation of aliphatic C-H bonds on polymeric supports

Tetrahedron

Volumn 53, Issue 19, 1997, Pages 6645-6652

  Jung, Kyung Woon ^a   Zhao, Xu Yang ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; POLYMER;

CHEMICAL STRUCTURE; CONFERENCE PAPER; DESULFURIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0030896381     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00222-6     Document Type: Conference Paper

References (31)

1. (a) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
2. (b) DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
3. For recent reports on combinatorial chemistry, see: (a) Baum, R. M. C&EN Feb. 7, 1994, 20.
4. (b) Borman, S. C&EN Feb. 12, 1996, 29.
5. For recent reviews, see: (c) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1385.
6. (d) Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 10779.
7. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
8. (f) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
9. (g) Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery, I.M. Chaiken, K.D. Janda, Eds., American Chemical Society, 1996.
10. For various examples, see reference 2. For recent examples, see: (a) Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333.
11. (b) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
12. (c) Morphy, J. R.; Rankovic, Z.; Rees, D. C. Tetrahedron Lett. 1996, 37, 3209.
13. (d) Barn, D. R.; Morphy, J. R.; Rees, D. C. Tetrahedron Lett. 1996, 37, 3213.
14. (e) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031.
15. (a) Sucholeiki, I. Tetrahedron Lett. 1994, 35, 7307.
16. (b) Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 1 1999.
17. (c) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006.
18. (d) Dinh, T. Q.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1161.
19. The liquid phase protocol has emerged as a promising alternative to currently used solid phase synthesis technologies: (a) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419.
20. (b) Service, R. F. Science 1996, 272, 1266.
21. For a recent review on polyethylene glycol polymers, see: (c) Zalipsky, S. Bioconjugate Chem. 1995, 6, 150.
22. Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, in press.
23. For thiol-disulfide interchange, see: (a) Lamoureux, G. V.; Whitesides, G. M. J. Org. Chem. 1993, 58, 633.
24. (b) Lees, W. J.; Whitesides, G. M. J. Org. Chem. 1993, 58, 642.
25. For reviews on thiols, see: (c) The chemistry of the thiol group; Patai, S., Ed.; John Wiley & Sons: New York, 1974; part 1 and part 2.
26. (a) Cleland, W. W. Biochemistry 1964, 3, 480.
27. (b) Guidot, J. P.; Le Gall, T. J. Org. Chem. 1993, 58, 5271.
28. (c) Martin, S. F.; Josey, J. A.; Wong, Y.-L.; Dean, D. W. J. Org. Chem. 1994, 59, 4805.
29. Linker 8 was extremely resistant to air oxidation, while 11 was slightly prone to oxidation (less than 5% over 3-4 weeks).
30. For a review, see: Pettit, G.; van Tamelen, E. E. Org. React. 1975, 12, 356.
31. All investigated disulfides were not appropriate for alkylation to take place. For example, MeO-PEG thiol 19 was prepared utilizing similar methods described (vide supra), however, alkylation did not take place presumably due to the electron deficiency of this thiol nucleophile.