Orthogonality and compatibility between Tsc and Fmoc amino-protecting groups

Tetrahedron

Volumn 61, Issue 9, 2005, Pages 2493-2503

  Choi, Jin Seok ^a   Kang, Hunhui ^a   Jeong, Nakcheol ^a   Han, Hogyu ^a  

^a Korea University   (South Korea)

Author keywords

Amino protecting group; Branched peptide; Fmoc; Orthogonal deprotection; Tsc

Indexed keywords

AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; LYSINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEPROTECTION REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS;

EID: 13644267757     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.052     Document Type: Article

References (36)

1. J.S. Choi, Y. Lee, E. Kim, N. Jeong, H. Yu, and H. Han Tetrahedron Lett. 44 2003 1607 1610
2. J.S. Choi, H.-S. Lee, Y. Lee, N. Jeong, H.-J. Kim, Y.-D. Kim, and H. Han Tetrahedron Lett. 43 2002 4295 4299
3. E.K. Liebler, and U. Diederichsen Org. Lett. 6 2004 2893 2896
4. C.J. Bosques, and B. Imperiali J. Am. Chem. Soc. 125 2003 7530 7531
5. K.A. Stephenson, S.R. Banerjee, T. Besanger, O.O. Sogbein, M.K. Levadala, N. McFarlane, J.A. Lemon, D.R. Boreham, K.P. Maresca, J.D. Brennan, J.W. Babich, J. Zubieta, and J.F. Valliant J. Am. Chem. Soc. 126 2004 8598 8599
6. T. Opatz, and R.M.J. Liskamp Org. Lett. 3 2001 3499 3502
7. R. Yang, M. Prorok, F.J. Castellino, and D.P. Weliky J. Am. Chem. Soc. 126 2004 14722 14723
8. A. Hamzé, J. Martinez, and J.-F. Hernandez J. Org. Chem. 69 2004 8349 8402
9. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 Wiley New York, NY
10. F. Albericio Biopolymers 55 2000 123 139
11. D. Orain, J. Ellard, and M. Bradley J. Comb. Chem. 4 2002 1 16
12. J.J. Díaz-Mochón, L. Bialy, and M. Bradley Org. Lett. 6 2004 1127 1129
13. B.W. Bycroft, W.C. Chan, S.R. Chhabra, P.H. Teesdale-Spittle, and P.M. Hardy J. Chem. Soc., Chem. Commun. 1993 776 777
14. B.W. Bycroft, W.C. Chan, S.R. Chhabra, and N.D. Hone J. Chem. Soc., Chem. Commun. 1993 778 779
15. H. Kunz Angew. Chem., Int. Ed. Engl. 26 1987 294 308
16. S.C. Miller, and T.S. Scanlan J. Am. Chem. Soc. 119 1997 2301 2302
17. S.C. Miller, and T.S. Scanlan J. Am. Chem. Soc. 120 1998 2690 2691
18. L.A. Carpino, and E.M.E. Mansour J. Org. Chem. 64 1999 8399 8401
19. M. Planas, E. Bardají, K.J. Jensen, and G. Barany J. Org. Chem. 64 1999 7281 7289
20. B.M. Kim, and J.H. Cho Tetrahedron Lett. 40 1999 5333 5336
21. E.E. Baird, and P.B. Dervan J. Am. Chem. Soc. 118 1996 6141 6146
22. M. Bodanszky, S.S. Deshmane, and J. Martinez J. Org. Chem. 44 1979 1622 1625
23. T. Young, and L.L. Kiessling Angew. Chem., Int. Ed. 41 2002 3449 3451
24. S. Liu, C. Dockendorff, and S.D. Taylor Org. Lett. 3 2001 1571 1574
25. T.R. Burke Jr., M.S. Symth, A. Otaka, and P.P. Roller Tetrahedron Lett. 34 1993 4125 4128
26. B. Ye, M. Akamatsu, S.E. Shoelson, G. Wolf, S. Giorgetti-Peraldi, X. Yan, P.P. Roller, and T.R. Burke Jr. J. Med. Chem. 38 1995 4270 4275
27. M. Ueki, and M. Amemiya Tetrahedron Lett. 28 1987 6617 6620
28. X. Li, T. Kawakami, and S. Aimoto Tetrahedron Lett. 39 1998 8669 8672
29. X. Bu, G. Xie, C.W. Law, and Z. Guo Tetrahedron Lett. 43 2002 2419 2422
30. X. Bu, X. Wu, G. Xie, and Z. Guo Org. Lett. 4 2002 2893 2895
31. X. Wu, X. Bu, K.M. Wong, W. Yan, and Z. Guo Org. Lett. 5 2003 1749 1752
32. J. Farrera-Sinfreu, M. Royo, and F. Albericio Tetrahedron Lett. 43 2002 7813 7815
33. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 5th ed. 2001 Wiley New York, NY pp 1331-1332
34. 2 at room temperature for 8 h.
35. E. Vedejs, and C. Kongkittingam J. Org. Chem. 65 2000 2309 2318
36. S.B.H. Kent Annu. Rev. Biochem. 57 1988 957 989