Allylic protection of thiols and cysteine: II: The N-[2,3,5,6- tetrafluoro-4-(N'-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group

Tetrahedron

Volumn 55, Issue 22, 1999, Pages 6945-6960

  Gomez Martinez, Paloma ^a   Kimbonguila, André Malanda ^a   Guibé, François ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYSTEINE; THIOL; THIOL DERIVATIVE;

ACIDITY; ALKALINITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; PROTECTION; SYNTHESIS;

EID: 0033612117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00323-3     Document Type: Article

References (16)

1. Preceding paper in this issue.
2. Weygand, F; Steglich W.; Pietta P. Chem. Ber. 1967, 100, 3841-3849.
3. Weygand, F.; Pietta P. Tetrahedron Lett. 1966, 44, 3751-3754.
4. Weygand, F.; Steglich, W.; Bjarnason, J.; Akhtar, R.; Khan, N. Tetrahedron Lett. 1966, 44, 3483-3487.
5. Malanda Kimbonguila, A. Mise au Point de Groupements Protecteurs Allyliques pour les Chaînes Latérales de L'histidine, de la Cystéine et de la Sérine en Vue D'application en Synthèse Peptidique. University of Paris-Sud (Orsay), 1966.
6. Evans, D. A.; Mathre, D. J.; Scott, W. L. J. Org. Chem. 1985, 50, 1830-1835.
7. Arnould, J. C; Landier F.; Pasquet, M. J. Tetrahedron Lett. 1992, 33, 7133-7136.
8. Kunz, H.; Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1984, 23, 436-437.
9. 5
10. Dessolin, M.; Guillerez, M.-G.; Thieriet, N.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1995, 32, 5741-5744.
11. Kunz, H.; März, J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1375-1377.
12. Indeed, as just pointed out before, additional treatment with acetic acid/2-mercaptoethanol is usually necessary to bring this fragmentation process (which in addition may be an equilibrium) to completion.
13. Fields, G. B.; Zhenping Tian, Barany, G: Principles and practice of solid-phase peptide synthesis. In Synthetic Peptides, A User's Guide; G. A. Grant, W. H., Ed.; Freeman and Company: New York, 1992; pp. 77-183.
14. Lloyd-Williams, P; Albericio, F. and Giralt, E.: Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, New-York, 1997; pp. 39-40 and 209-231.
15. Stelekatos, G. C.; Paganou, A.; Zervas, L. J. Chem. Soc. C 1966, 1191-1199.
16. See for instance: Coste, J.; Dufour, M.-N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 31, 669-672.