Stereoselective synthesis of new modified conformationally constrained L-tyrosine analogue with potential applications to SH2 domain ligands

Tetrahedron

Volumn 61, Issue 21, 2005, Pages 4971-4981

  Liu, Fa ^a   Hu, Tai Shan ^a   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

L Tyrosine; Mannich reaction; Src homology 2

Indexed keywords

PROTEIN SH2; TYROSINE DERIVATIVE;

ALKYLATION; ARTICLE; CONFORMATION; COVALENT BOND; CYCLIZATION; FRIEDEL CRAFTS REACTION; MANNICH REACTION; MICHAEL ADDITION; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 18144410939     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.042     Document Type: Article

References (18)

1. T.R. Burke Jr., J.J. Barchi Jr., C. George, G. Wolf, S.E. Shoelson, and X. Yan J. Med. Chem. 38 1995 1386 1396
2. H. Josien, S. Lavielle, A. Brunissen, M. Saffroy, Y. Torrens, J.C. Beaujouan, J. Glowinski, and G. Chassaing J. Med. Chem. 37 1994 1586 1601
3. D. Jiao, K.C. Russell, and V.J. Hruby Tetrahedron 49 1993 3511 3520
4. H.I. Mosberg, A.L. Lomize, C.G. Wang, H. Kroona, D.L. Heyl, K. Sobczykkojiro, W.L. Ma, C. Mousigian, and F. Porreca J. Med. Chem. 37 1994 4371 4383
5. D. Obrecht, C. Lehmann, R. Ruffieux, P. Schonholzer, and K. Muller Helv. Chim. Acta 78 1995 1567 1587
6. R.B. Birge, and H. Hanafusa Science 262 1993 522
7. L. Tong, T.C. Warren, J. King, R. Betageri, and S. Jakes J. Mol. Biol. 256 1996 601
8. X.-Z. Wang, Z.-J. Yao, H. Liu, M. Zhang, D. Yang, C. George, and R.T. Burke Jr. Tetrahedron 59 2003 6087
9. B. Ye, Z. Yao, and T.R. Burke Jr. J. Org. Chem. 62 1997 5428
10. F. Liu, J. Jiao, H. Zha, and Z. Yao Chin. J. Chem. 22 2004 1022 1028
11. F. Liu, H-Y. Zha, and Z.-J. Yao J. Org. Chem. 68 2003 6679
12. M. Otsuka, T. Masuda, A. Haupt, and O. Masaji J. Am. Chem. Soc. 112 1990 838 845
13. C.M. Acevedo, E.F. Kogut, and M.A. Lipton Tetrahedron 57 2001 6353 6359
14. C. Herdeis, and H.P. Hubmann Tetrahedron: Asymmetry 3 1994 351 354
15. Formation of the two-time Michael addition product:
16. If 8 was treated with TBAF, Boc immigration occurred in high conversion.
17. CCDC 264692 & 264693 contain the supplementary crystallographic data for compounds 25 and 11, respectively, in this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
18. The Wittig reagent was prepared by treating the corresponding phosphonium salt with aq. NaOH solution. If the excess NaOH was not washed off completely, the olefin product of the Witting reaction maybe partly racemize because of the base.