The (2-phenyl-2-trimethylsiylyl)ethyl (PTMSE) ester - A carboxy protecting group cleavable under neutral conditions;Der (2-phenyl-2-trimethylsilyl)ethyl-(PMTSE)-ester - Eine neutral spaltbare carboxyschutzgruppe

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 57, Issue 8, 2002, Pages 928-936

  Wagner, Michael ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Carboxy Protecting Group; Fluoride Induced Elimination; Peptides

Indexed keywords

CONDENSATION REACTIONS; DICHLOROMETHANE; FLUORINE COMPOUNDS; PEPTIDES;

ALLYLOXYCARBONYL; BENZYL ESTERS; BOC GROUP; FLUORIDE-INDUCED ELIMINATION; NEUTRAL CONDITIONS; PROTECTING GROUP; TETRABUTYLAMMONIUM FLUORIDES;

ESTERS;

AMINO ACID; CARBONYL DERIVATIVE; DICHLOROMETHANE; ESTER DERIVATIVE; FLUORIDE; PALLADIUM; PEPTIDE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; DEGRADATION; HYDROLYSIS; MOLECULAR STABILITY; POLYMERIZATION;

EID: 0036700364     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2002-0814     Document Type: Article

References (26)

1. Übersichten s. z.B.: a) J. S. Früchtel, G. Jung, Angew. Chem. 108, 19 (1996); Angew. Chem. Int. Ed. Engl. 35, 17 (1996); b) F. Schweitzer, O. Hindsgaul, Curr. Opin. Chem. Biol. 3, 291 (1999).
2. Übersichten s. z.B.: a) J. S. Früchtel, G. Jung, Angew. Chem. 108, 19 (1996); Angew. Chem. Int. Ed. Engl. 35, 17 (1996); b) F. Schweitzer, O. Hindsgaul, Curr. Opin. Chem. Biol. 3, 291 (1999).
3. Übersichten s. z.B.: a) J. S. Früchtel, G. Jung, Angew. Chem. 108, 19 (1996); Angew. Chem. Int. Ed. Engl. 35, 17 (1996); b) F. Schweitzer, O. Hindsgaul, Curr. Opin. Chem. Biol. 3, 291 (1999).
4. a) P. J. Kocienski, Protecting Groups, Thieme Verlag Stuttgart, New York (1994); b) T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3. Aufl., J. Wiley, New York (1999).
5. a) P. J. Kocienski, Protecting Groups, Thieme Verlag Stuttgart, New York (1994); b) T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3. Aufl., J. Wiley, New York (1999).
6. O. Seitz, ChemBioChem. 1, 214 (2000).
7. a) P. Sieber, Helv. Chim. Acta 60, 2711 (1977); b) E. Wünsch, L. Moroder, O. Keller, Hoppe Seylers Z. Physiol. Chem. 362, 1289 (1981).
8. a) P. Sieber, Helv. Chim. Acta 60, 2711 (1977); b) E. Wünsch, L. Moroder, O. Keller, Hoppe Seylers Z. Physiol. Chem. 362, 1289 (1981).
9. H. Gerlach, Helv. Chim. Acta 60, 3039 (1977).
10. B. M. Lipshutz, J. J. Pegram, Tetrahedron Lett. 21, 3343 (1980).
11. W. Bernhard, I. Flemming, J. Organomet. Chem. 271, 281 (1984).
12. L. A. Carpino, G. Y. Han, J. Am. Chem. Soc. 92, 5748 (1972).
13. M. Ueki, M. Amemiya, Tetrahedron Lett. 28, 6617 (1987).
14. H.-G. Chao, M. S. Bernatowicz, P. D. Reiss, C. E. Klimas, G. R. Matsueda, J. Am. Chem. Soc. 116, 1746 (1994).
15. M. Wagner, H. Kunz, Synlett 400 (2000).
16. A. E. Bey, D. R. Weyenberg, J. Org. Chem. 31, 2036 (1966).
17. F. Hayakawa, S. Watnabe, N. Shimizu, Y. Tsuno, Bull. Chem. Soc. Jpn. 66, 153 (1993).
18. a) J. J. Eisch, J. E. Galle, J. Org. Chem. 41, 2615 (1976); b) J. J. Eisch, J. E. Galle, J. Organomet. Chem. 341, 293 (1988); c) T-L. Chow, Hua Hsüeh Hsüeh Pao, Chem. Abstr. 24, 426 (1958).
19. a) J. J. Eisch, J. E. Galle, J. Org. Chem. 41, 2615 (1976); b) J. J. Eisch, J. E. Galle, J. Organomet. Chem. 341, 293 (1988); c) T-L. Chow, Hua Hsüeh Hsüeh Pao, Chem. Abstr. 24, 426 (1958).
20. a) J. J. Eisch, J. E. Galle, J. Org. Chem. 41, 2615 (1976); b) J. J. Eisch, J. E. Galle, J. Organomet. Chem. 341, 293 (1988); c) T-L. Chow, Hua Hsüeh Hsüeh Pao, Chem. Abstr. 24, 426 (1958).
21. B. Neises, W. Steglich, Angew. Chem. 90, 556 (1978), Angew. Chem. Int. Ed. Engl. 17, 522 (1978).
22. B. Neises, W. Steglich, Angew. Chem. 90, 556 (1978), Angew. Chem. Int. Ed. Engl. 17, 522 (1978).
23. H. Kunz, C. Unverzagt, Angew. Chem. 96, 436 (1984); Angew. Chem. Int. Ed. Engl. 23, 426 (1984).
24. H. Kunz, C. Unverzagt, Angew. Chem. 96, 436 (1984); Angew. Chem. Int. Ed. Engl. 23, 426 (1984).
25. L. A. Carpino, A. El-Faham, F. Albericio, Tetrahedron Lett. 35, 2279 (1994).
26. G. Breipohl, W. König (Höchst AG), European Patent EP-A 0460446, A1, 23.5.1990.