Tetrachlorophthaloyl as a versatile amine protecting group

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 432-433

  Debenham, John S ^a   Fraser Reid, Bert ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000557626     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951943v     Document Type: Article

References (23)

1. The use of TCP group for amine protection in oligosaccharide synthesis was first reported (J. S Debenham and B. Fraser-Reid) at the XVIIth International Carbohydrate Symposium, Ottawa, Canada, July 1994, paper B1.38, and subsequently (J. S. Debenham and B. Fraser-Reid) at the 209th National Meeting of the American Chemical Society, Anaheim, CA, April 1995, paper CARB 008.
2. The use of TCP group for amine protection in oligosaccharide synthesis was first reported (J. S Debenham and B. Fraser-Reid) at the XVIIth International Carbohydrate Symposium, Ottawa, Canada, July 1994, paper B1.38, and subsequently (J. S. Debenham and B. Fraser-Reid) at the 209th National Meeting of the American Chemical Society, Anaheim, CA, April 1995, paper CARB 008.
3. Debenham, J. S.; Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Am. Chem. Soc., 1995, 117, 3302-3303.
4. (a) Lemieux, R.; Takeda, T.; Chung, B. In Synthetic Methods for Carbohydrate; El Khadem, H. S., Ed.; ACS Symposium Series: Washington, DC, 1976; Vol. 39, pp 90-115.
5. (b) Ing, H.; Manske, R. J. Chem. Soc. 1926, 2348-2351.
6. Zehavi, U. J. Org. Chem. 1977, 42, 2819-2821.
7. (a) Barney, G.; Merrifield, R. B. J. Am. Chem. Soc. 1977, 99, 7363-7365.
8. (b) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans, 1 1995, 405-415.
9. For example; see the chapters on protection of amino groups in the most extensive of two recent source books: (a) Protecting Groups; Kocienski, P. J., Ed.; Thieme:Stuttgart, 1994; Chapter 6. (b) Protecting Groups in Organic Synthesis, 2nd ed.; Greene, T. W., Wuts, P. G. M., Eds.; John Wiley & Sons, Inc.: New York, 1991; Chapter 7.
10. For example; see the chapters on protection of amino groups in the most extensive of two recent source books: (a) Protecting Groups; Kocienski, P. J., Ed.; Thieme:Stuttgart, 1994; Chapter 6. (b) Protecting Groups in Organic Synthesis, 2nd ed.; Greene, T. W., Wuts, P. G. M., Eds.; John Wiley & Sons, Inc.: New York, 1991; Chapter 7.
11. Garg, H. G.; von dem Bruch, K.; Kunz, H. Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed.; Academic Press, Inc.: San Diego, 1994; Vol. 50, pp 277-310.
12. Kjellén, L.; Lindahl, U., Annu. Reu. Biochem. 1991, 60, 443-475. Hassell, John R.; Kimura, James H; Hascall, Vincent C. Annu. Rev. Biochem. 1986, 55, 539-567.
13. Kjellén, L.; Lindahl, U., Annu. Reu. Biochem. 1991, 60, 443-475. Hassell, John R.; Kimura, James H; Hascall, Vincent C. Annu. Rev. Biochem. 1986, 55, 539-567.
14. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 5343-5346.
15. TCP is the cheapest of a group of deactivated phthalides, including mononitro and mono- and dihalo. Additionally, many of the TCP derivatives that we have prepared tend to crystallize readily, the attendant advantages for large scale work being obvious.
16. (a) Handlon, A L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797.
17. (b) Ratcliffe, A. J.; Konradson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1990, 112, 5665-5666.
18. Fraser-Reid, B.; Udodong, U.; Wu. Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett. 1992, 927-942.
19. Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243, 139-164.
20. It is worth noting that the ethylenediamine-based cleavage product's lack of solubility makes it difficult to positively characterize.
21. Wessel, H.-P.; Iverson, T; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247-2250.
22. It should be noted that the TCP group is unstable to the strongly basic conditions necessary for standard NaH/BnBr benzylations.
23. Whether this reactivity difference can be leveraged into an armed/disarmed protocol for amino acceptors is currently being tested in our laboratories.