Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Journal of Organic Chemistry

Volumn 72, Issue 1, 2007, Pages 299-302

  Yan, Ming Chung ^a,b   Chen, Yeng Nan ^a   Wu, Huan Ting ^a   Lin, Chang Ching ^a,b   Chen, Chien Tien ^c   Lin, Chun Cheng ^a,b  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b GENOMICS RESEARCH CENTER   (Taiwan)

^c NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; ORGANIC SOLVENTS; OXIDATION;

ALCOHOLYSIS; GLYCOSIDIC BOND CLEAVAGE; SULFIDES;

CARBOHYDRATES;

CARBOHYDRATE; MONOSACCHARIDE; SOLVENT; TRIFLUOROMETHANESULFONIC ACID; VANADIUM DERIVATIVE; VANADYL DERIVATIVE; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ACIDS; ALKENES; BENZYLIDENE COMPOUNDS; CARBOHYDRATES; CATALYSIS; MESYLATES; MOLECULAR STRUCTURE; VANADATES; WATER;

EID: 33846089854     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061881g     Document Type: Article

References (47)

1. (a) Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis, 3rd ed.; Wiley & Sons: New York, 1999.
2. (b) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York, 2004.
3. (a) Crich, D.; Yao, Q. J. Am. Chem. Soc. 2004, 126, 8232-8236.
4. (b) Crich, D.; Li, W.; Li, H. J. Am. Chem. Soc. 2004, 126, 15081-15086.
5. (c)Clode, D. M. Chem. Rev. 1979, 79, 491-513.
6. (d) Andrews, C. W.; Rodebaugh, R.; Frase-Reid, B. J. Org. Chem. 1996, 61, 5280-5289.
7. (e) Russell, R. N.; Weigel, T. M.; Han, O.; Liu, H.-W. Carbohydr. Res. 1990, 201, 95-114.
8. (a) Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 95-98.
9. (b) Hirama, M.; Node, T.; Yasuda, S.; Ito, S. J. Am. Chem. Soc. 1991, 113, 1830-1832.
10. (a) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
11. (b) Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. H. Tetrahedron Lett. 1981, 22, 3455-3458.
12. (c) Clark, J. H. Chem. Rev. 1980, 80, 429-452.
13. (a) Bessodes, M.; Komiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579-580.
14. (b) Blickenstaff, R. T. J. Am. Chem. Soc. 1960, 82, 3673-3676.
15. (c) Choy, Y. M.; Unrau, A. M. Carbohydr. Res. 1971, 17, 439-443.
16. (d) Martin, S. F.; Dodge, J. A.; Burgess, L. E.; Hartmann, M. J. Org. Chem. 1992, 57, 1070-1072.
17. (e) Angyal, S. J.; Beveridge, R. J. Carbohydr. Res. 1978, 65, 229-234.
18. (a) Cabaret, D.; Wakselman, M. Can. J. Chem. 1990, 68, 2253-2257.
19. (b) Lampe, T. F. S.; Hoffmann, H. M. R. Tetrahedron Lett. 1996, 37, 7695-7698.
20. (c) Tewson, T. J.; Welch, M. J. J. Org. Chem. 1978, 43, 1090-1092.
21. (a) Barone, G.; Bedini, E.; Iadonisi, A.; Manzo, E.; Parrilli, M. Synlett 2002, 1645-1648.
22. (b) Ramalingam, T.; Srinivas, R.; Reddy, B. V. S.; Yadav, J. S. Synth. Commun. 2001, 31, 1091-1095.
23. (c) Chen, M.-Y.; Lu, K.-C.; Lee, Adam S.-Y.; Lin, C.-C. Tetrahedron Lett. 2002, 43, 2777-2780.
24. (d) Chen, M.-Y.; Patkar, L. N.; Lu, K.-C.; Adam, S.-Y.; Lin, C.-C. Tetrahedron 2004, 60, 11465-11475.
25. McCass, M.; Cameron, D. J. Carbohydr. Res. 1978, 60, 206-209.
26. (a) Togni, A. Organometallics 1990, 9, 3106-3133.
27. (b) Chen, C.-T.; Hon, S.-W.; Weng, S.-S. Synlett 1999, 816-818.
28. (a) Lattanzi, A.; Leadbeater, N. E. Org. Lett. 2002, 4, 1519-1521.
29. (b) Jorgensen, K. A. Chem. Rev. 1989, 89, 431-458.
30. (a) Hon, S.-W.; Li, C-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872.
31. (b) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532.
32. (a) Chen, C.-T.; Kuo, J.-H.; Li, C.-H., Barhate, N. B.; Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.; Lin, J.-S.; Lin, C.-J.; Chou, Y.-C. Org. Lett. 2001, 3, 3729-3732.
33. (b) Chen, C.-T.; Kuo, J.-H.; Pawar, V. D.; Munot, Y. S.; Weng, S.-S.; Ku, C.-H.; Liu, C.-Y. J. Org. Chem. 2005, 70, 1188-1197.
34. (c) Chen, C.-T.; Kuo, J.-H.; Ku, C.-H.; Weng, S.-S.; Liu, C.-Y. J. Org. Chem. 2005, 70, 1328-1339.
35. Chen, C.-T.; Weng, S.-S.; Kao, J.-Q.; Lin, C.-C.; Jan, M.-D. Org. Lett. 2005, 7, 3343-3346.
36. Lin, C.-C.; Jan, M.-D.; Weng, S.-S.; Lin, C.-C.; Chen, C.-T. Carbohydr. Res. 2006, 341, 1948-1953.
37. Carbohydrates in Chemical Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1.
38. (a) Demchenko, A. V.; Boons, G. -J. Chem. Eur. J. 1999, 5, 1278-1283.
39. (b) Demchenko, A. V.; Boons, G. -J. Tetrahedron Lett. 1998, 39, 3065-3068.
40. (c) Yu, C.-S.; Niikura, K.; Lin, C.-C.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 2900-2903.
41. (d) Tanaka, H.; Adachi, M.; Takahashi, T. Chem. Eur. J. 2005, 11, 849-862.
42. (e) Adachi, M.; Tanaka, H.; Takahashi, T. Synlett 2004, 609-614.
43. (f) Ando, H.; Koike, Y.; Ishida, H.; Kiso, M. Tetrahedron Lett. 2003, 44, 6883-6886.
44. (g) Pan, Y.; Chefalo, P.; Nagy, N.; Harding, C.; Guo, Z. J. Med. Chem. 2005, 48, 875-883.
45. (h) Meijer, A.; Ellervik, U. J. Org. Chem. 2004, 69, 6249-6256.
46. (i) De, Meo, C.; Demchenko, A. V.; Boons, G.-J. J. Org. Chem. 2001, 66, 5490-5497.
47. Krecknerhova, M.; Seela, F. Nucleosides Nucleotides 1992, 11, 1393-1396.