N-tetrachlorophthaloyl (TCP) for ready protection/deprotection of amino sugar glycosides

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 11, 1996, Pages 1909-1918

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

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; GLYCOSIDE; OLIGOSACCHARIDE;

CONFERENCE PAPER; SYNTHESIS;

AMINO SUGARS; GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; PHTHALIC ACIDS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0030293910     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(96)00173-3     Document Type: Conference Paper

References (35)

1. 1. Kocienski, P.J. Protecting Groups; Thieme: Stuttgart, 1994, Chapter 6; Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis; John Wiley & Sons: New York, 2nd Ed., 1991, Chapter 7.
2. 1. Kocienski, P.J. Protecting Groups; Thieme: Stuttgart, 1994, Chapter 6; Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis; John Wiley & Sons: New York, 2nd Ed., 1991, Chapter 7.
3. 2. Garg, H. G.; von dem Bruch, K.; Kunz, H. Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed., Academic: San Diego, 1994: Vol. 50, pp 277-310; Kjellén, Lena; Lindahl, U. Annu. Rev. Biochem. 1991, 60, 443-475; Hassell, J. R.; Kimura, J. H.; Hascall, V. C. Annu. Rev. Biochem. 1986, 55, 539.
4. 2. Garg, H. G.; von dem Bruch, K.; Kunz, H. Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed., Academic: San Diego, 1994: Vol. 50, pp 277-310; Kjellén, Lena; Lindahl, U. Annu. Rev. Biochem. 1991, 60, 443-475; Hassell, J. R.; Kimura, J. H.; Hascall, V. C. Annu. Rev. Biochem. 1986, 55, 539.
5. 2. Garg, H. G.; von dem Bruch, K.; Kunz, H. Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed., Academic: San Diego, 1994: Vol. 50, pp 277-310; Kjellén, Lena; Lindahl, U. Annu. Rev. Biochem. 1991, 60, 443-475; Hassell, J. R.; Kimura, J. H.; Hascall, V. C. Annu. Rev. Biochem. 1986, 55, 539.
6. 3. See for example: Bochkov, A. F.; Zaikov, G. E. Chemistry of the O-Glycosode Bond; Pergamon: Oxford, 1979, Chapter 2; Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 97, 1167.
7. 3. See for example: Bochkov, A. F.; Zaikov, G. E. Chemistry of the O-Glycosode Bond; Pergamon: Oxford, 1979, Chapter 2; Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 97, 1167.
8. 4. Campbell, A.S.; Fraser-Reid, B. Bioorg. Med. Chem. 1994, 2, 1209; Campbell, A.S.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 10387.
9. 4. Campbell, A.S.; Fraser-Reid, B. Bioorg. Med. Chem. 1994, 2, 1209; Campbell, A.S.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 10387.
10. 5. Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 7920.
11. 6. Fraser-Reid, B.; Udodong, U.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett. 1992, 927.
12. 7. Wu, Z.; Mootoo, D. R.; Fraser-Reid, B. Tetrahedron Lett. 1988, 29, 6549.
13. 8. Madsen, R.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 772.
14. 9. Lemieux, R.; Takeda, T.; Chung, V Synthetic Methods for Carbohydrates; El Khadem, H. S., Ed., ACS Symposium Series: Washington, DC 1976, Vol. 39, pp 90-115.
15. 10. For example see: Spijker, N. M.; Westerduin, P.; van Boeckel, C. A. A. Tetrahedron 1992, 48, 6297; Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061; Koeman, F. A. W.; Meissner, J. W. G.; van Ritter, H. R. P.; Kamerling, J. P.; Vliegenthart, J. F. G. J. Carbohydr. Chem. 1994, 13, 1.
16. 10. For example see: Spijker, N. M.; Westerduin, P.; van Boeckel, C. A. A. Tetrahedron 1992, 48, 6297; Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061; Koeman, F. A. W.; Meissner, J. W. G.; van Ritter, H. R. P.; Kamerling, J. P.; Vliegenthart, J. F. G. J. Carbohydr. Chem. 1994, 13, 1.
17. 10. For example see: Spijker, N. M.; Westerduin, P.; van Boeckel, C. A. A. Tetrahedron 1992, 48, 6297; Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061; Koeman, F. A. W.; Meissner, J. W. G.; van Ritter, H. R. P.; Kamerling, J. P.; Vliegenthart, J. F. G. J. Carbohydr. Chem. 1994, 13, 1.
18. 11. Ing, H.; Manske, R. J. Chem. Soc. 1926, 2348.
19. 12. Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243, 139 and references cited therein.
20. 13. Handlon, A, L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796.
21. 14. Osby, J. A.; Martin, M. G.; Ganem, B. Tetrahedron Lett. 1984, 25, 2093.
22. 15. Dasgupta, F.; Garegg, P. J. Carbohydr. Chem. 1988, 7, 701; Ito, Y.; Sato, S.; Mori, M., Ogawa, T. J. Carbohydr. Chem. 1988, 7, 359.
23. 15. Dasgupta, F.; Garegg, P. J. Carbohydr. Chem. 1988, 7, 701; Ito, Y.; Sato, S.; Mori, M., Ogawa, T. J. Carbohydr. Chem. 1988, 7, 359.
24. 2 substitution on phthalimides at the 4-position had on benzylamine derivatives. Tsubouchi, H.; Tsuji, K.; Ishikawa, H. Synlett. 1994, 63.
25. 17. The prices shown are from a recent Aldrich catalog.
26. 18. Shimizu et al. have recently reported a study on the less base-sensitive 4,5-dichlorophthalimido group. Shimizu, H., Ito, Y., Matsuzaki, Y., Iijima, H., Ogawa, T. Biosci. Biotech. Biochem. 1996, 60, 73.
27. 19. Wessel, H.-P.; Iverson, T; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
28. 20. Capon, B. Chem. Rev. 1969, 69, 407.
29. 21. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 5343. See also N,N-diacetyl protection which, however, requires more basic conditions (NaOMe/MeOH) for removal. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 6871.
30. 21. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 5343. See also N,N-diacetyl protection which, however, requires more basic conditions (NaOMe/MeOH) for removal. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 6871.
31. 22. Jensen, K. J., Hansen, P. R., Venugopal, D., Barany, G. J. Am. Chem. Soc. 1996, 118, 3148.
32. 23. Meinjohanns, E.; Meldal, M.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin. Trans. 1 1995, 405-415.
33. 24. Barany, G.; Merrifield, R.B. J. Am. Chem. Soc. 1977, 99, 7363.
34. 25. This solvent system dissolves every TCP substrate we have encountered. TCP cleavages can be effected either with or without a protic cosolvent.
35. 26. Merritt, J. R.; Debenham, J. S.; Fraser-Reid, B. J. Carbohydr. Chem. 1996, 15, 1, 65.