Synthetic studies on threonines. The preparation of protected derivatives of D-allo- and L-allo-threonine for peptide synthesis

Tetrahedron

Volumn 53, Issue 9, 1997, Pages 3369-3382

  Lloyd Williams, Paul ^a   Sánchez, Agustí ^a   Carulla, Natàlia ^a   Ochoa, Teresa ^a   Giralt, Ernest ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; THREONINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550878     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00059-8     Document Type: Article

References (23)

1. 1. Hamann, M. T., Scheuer P. J., J. Am. Chem. Soc., 1993, 115, 5825.
2. 2. Rinehart, K. L., Holt, T. G., Fregeau, N. L., Keifer, P. A., Wilson, G. R., Perun, T. J., Sakai, R., Thompson, A. G., Stroh, J. G., Shield, L. S., Seigler, D. S., Li, L. H., Martin, D. G., Grimmelikhuijzen, C. J. P., Gäde, G., J. Nat. Prod., 1990, 53, 771.
3. 3. Wipf, P., Chem. Rev., 1996, 95, 2115.
4. 4. Goodman, M., Chorev, M., Acc. Chem. Res., 1979, 12, 1.
5. 5. Chorev, M., Goodman, M., Acc. Chem. Res., 1993, 26, 266.
6. 6. Pons, D., Savignac, M., Genet, J.-P., Tetrahedron Lett., 1990, 31, 5023.
7. 7. Beaulieu, P. L., Tetrahedron Lett., 1991, 32, 1031.
8. 8. Blaskovich, M. A., Lajoie, G. A., Tetrahedron Lett., 1993, 34, 3837.
9. 9. Jackson, R. F. W., Palmer, N. J., Wythes, M. J., Tetrahedron Lett., 1994, 35, 7433.
10. 10. Fischer, P. M., Sandosham, J., Tetrahedron Lett., 1995, 36, 5409.
11. 11. Sánchez, Y. M., Haack, T., González, M. J., Ludevid, M. D., Giralt, E., In Peptides. Chemistry, Structure and Biology. Proceedings of the 14th American Peptides Symposium, Kaumaya, P.T.P., Hodges, R.S., Eds., Mayflower Scientific Ltd, Kingswinford, UK, 1996, p. 558.
12. 12. Guichard, G., Muller, S., van Regenmortel, M., Briand, J. P., Mascagni, P., Giralt, E., Trends in Biotechnology, 1996, 14, 44.
13. 13. Lloyd-Williams, P., Albericio, F., Giralt, E., Chemical Approaches to the Synthesis of Peptides and Proteins, CRC Press, Boca Raton, FL, in press.
14. 14. Bodanszky, M., Martinez, J., Synthesis, 1981, 333.
15. 15. Lloyd-Williams, P., Carulla, N., Giralt, E., Tetrahedron Lett., in press.
16. 16. Lloyd-Williams P., Monerris, P., Gonzalez, I., Jou, G., Giralt, E., J. Chem. Soc., Perkin Trans. 1, 1994, 1969.
17. 17. Jou, G., González, I., Albericio, F., Lloyd-Williams, P., Giralt, E., J. Org. Chem., in press.
18. 18. Greenstein, J. P., Methods Enzymol. 1957, 3, 554.
19. 19. Chen, F. M. F., Kuroda, K., Benoiton, N. L., Synthesis, 1979, 230.
20. 20. Bodanszky, M., Bodanszky, A., The Practice of Peptide Synthesis, Springer Verlag, Berlin, 1984.
21. 21. Winitz, M., Bloch-Frankenthal, L., Izumiya, N., Birnbaum, S. M., Baker, C. G., Greenstein, J. P., J. Am. Chem. Soc., 1956, 78, 2423.
22. 22. Masaki, M., Kitahara, T., Kurita, H., Ohta, M., J. Am. Chem. Soc., 1968, 90, 4508.
23. 23. Buck, R. H., Krummen, K., J. Chromatogr., 1987, 387, 255.