A thermally-cleavable linker for solid-phase synthesis

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1181-1184

  Keller, Keith A ^a   Guo, Jianhua ^a   Punna, Sreenivas ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Cleavage; Linker; Peptides; Solid phase

Indexed keywords

BETA AMINO ACID; EPOXIDE; FURFURYL ALCOHOL; LEUCINE ENKEPHALIN; MALEIMIDE DERIVATIVE; NORBORNENE DERIVATIVE; RESIN; THIOPHENOL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; RING OPENING; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; THERMAL ANALYSIS;

EID: 12344323717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.067     Document Type: Article

References (25)

1. F. Gullier, D. Orain, and M. Bradley Chem. Rev. 100 2000 2091 2157
2. K. Gordon, and S. Balasubramanian J. Chem. Technol. Biotechnol. 74 1999 835 851
3. F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, and C. Zechel Angew. Chem., Int. Ed. Engl. 35 1996 2288 2337
4. B. Rickborn Org. React. 52 1998 1 393
5. B. Rickborn Org. React. 53 1998 223 629
6. M.-C. Lasne, and J.-L. Ripoll Synthesis 1985 121 143
7. Review: C.O. Kappe, S.S. Murphree, and A. Padwa Tetrahedron 53 1997 14179 14233
8. Other examples: M. Lautens, and T. Rovis Tetrahedron 54 1998 1107 1116
9. M. Lautens, A.C. Smith, A.S. Abd-El-Aziz, and A.H. Huboux Tetrahedron Lett. 31 1990 3253 3256
10. L. Blanco, R. Bloch, E. Bugnet, and S. Deloisy Tetrahedron Lett. 41 2000 7875 7878
11. See also: D.L. Whitehouse, K.H. Nelson, S.N. Savinov, R.S. Löwe, and D.J. Austin Bioorg. Med. Chem. 6 1998 1273 1282
12. H.E. Russell, R.W.A. Luke, and M. Bradley Tetrahedron Lett. 41 2000 5287 5290
13. X. Wang, J.J. Parlow, and J.A. Porco Org. Lett. 2 2000 3509 3512
14. B. Nie, K. Hasan, M.D. Greaves, and V.M. Rotello Tetrahedron Lett. 36 1995 3617 3618
15. R. Gheneim, C. Perez-Berumen, and A. Gandini Macromolecules 35 2002 7246 7253
16. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd Ed. 1999 John Wiley & Sons New York
17. O. Keller, and J. Rudinger Helv. Chem. Acta 58 2 1975 531 541
18. H.S. Byun, and R. Bittman Tetrahedron Lett. 30 1989 2751 2754
19. P.N. Guivisdalsky, and R.J. Bittman Org.Chem. 54 1989 4637 4642
20. M. Chini, P. Crotti, and F. Macchia Tetrahedron Lett. 31 1990 4661 4664
21. W.G. Dauben, J.Y.L. Lam, and Z.R. Guo J. Org. Chem. 61 1996 4816 4819
22. 3CN, MeOH, water, and MeOH, and then dried under vacuum. General method for the cleavage of resin-bound species: the substituted resin was taken up in approximately 100 mL of toluene and heated to reflux for 12 h. After cooling to room temperature the solvent was filtered away from the polymer and evaporated yielding the free maleimide. Overall yields for the three steps (Diels-Alder attachment, epoxide ring opening, resin cleavage) from 6 were in excess of 80%; product purities were established by NMR and HPLC
23. J.S. Morley Annu. Rev. Pharmacol. Toxicol. 20 1980 81 110
24. M.I. Davila-Garcia, and E.C. Azmitia Adv. Exp. Med. Biol. 265 1989 75 92
25. M. Rinnova, A. Nefzi, and R.A. Houghten Bioorg. Med. Chem. Lett. 12 2002 3175 3178