ZrCl4-catalyzed efficient ferrier glycosylation: A facile synthesis of pseudoglycals

Synthesis

Volumn , Issue 6, 2004, Pages 834-836

  Smitha, G ^a   Reddy, Ch Sanjeeva ^a  

^a KAKATIYA UNIVERSITY   (India)

Author keywords

Ferrier glycosylation; Pseudoglycals; Zirconium(IV) chloride

Indexed keywords

CATALYSIS; GLYCOLS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

GLYCOSYLATION; PSEUDOGLYCALS;

ZIRCONIUM COMPOUNDS;

ALCOHOL DERIVATIVE; GLUCONATE CALCIUM; GLYCOSIDE; THIOL DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG SYNTHESIS; GLYCOSYLATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 2342483630     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815974     Document Type: Article

References (46)

1. (a) Ferner, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570.
2. (b) For a recent review on the Ferner rearrangement, see: Ferner, R. J. Topics Curr. Chem. 2001, 215, 153.
3. (c) For review on glycosidation, see: Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
4. (a) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859.
5. (b) Schmidt, R. R.; Angerbauer, R. Carbohydr. Res. 1981, 89, 159.
6. (c) Schmidt, R. R.; Angerbauer, R. Carbohydr. Res. 1981, 89, 193.
7. (d) Schmidt, R. R.; Angerbauer, R. Carbohydr. Res. 1979, 72, 272.
8. (e) Bracherro, M. P.; Cabrera, E. F.; Gomez, G. M.; Peredes, L. M. R. Carbohydr. Res. 1998, 181, 308.
9. (f) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 120, 13515.
10. (g) Liu, Z. J. Tetrahedron: Asymmetry 1999, 10, 2119.
11. Williams, N. R.; Wander, J. D. The Carbohydrates. Chemistry and Biochemistry; Academic Press: New York, 1980, 761.
12. (a) Descotes, G.; Martin, J.-C. Carbohydr. Res. 1977, 56, 168.
13. (b) Klaffke, W.; Pudlo, P.; Springer, D.; Thiem, J. Liebigs-Ann. Chem. 1991, 6, 509.
14. (a) Grynkiewiez, G.; Priebe, W.; Zamojski, A. Carbohydr. Res. 1979, 68, 33.
15. (b) Bhate, P.; Horton, D.; Priebe, W. Carbohydr. Res. 1985, 144, 331.
16. Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M.; Konoshita, M. J. Chem. Soc., Chem. Commun. 1993, 704.
17. (a) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180.
18. (b) Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M. Tetrahedron Lett. 1994, 35, 5673.
19. Fraser-Reid, B.; Madsen, R. J. Org. Chem. 1995, 60, 3851.
20. (a) Babu, B. S.; Balasubramanian, K. K. Tetrahedron Lett. 1999, 40, 5777.
21. (b) Yadav, J. S.; Reddy, B. V. S.; Chandraiah, L.; Reddy, K. S. Carbohydr. Res. 2001, 332, 221.
22. Schmidt, R. R.; Hoffman, M. Tetrahedron Lett. 1982, 23, 409.
23. (a) Toshima, K.; Miyamoto, N.; Matsuo, G.; Nakata, M.; Matsumura, S. Chem. Commun. 1996, 1379.
24. (b) Shanmugasundaram, B.; Bose, A. K.; Balasubramanian, K. K. Tetrahedron Lett. 2002, 43, 6795.
25. Masson, C.; Soto, J.; Bessodes, M. Synlett 2000, 1281.
26. (a) Babu, B. S.; Balasubramanian, K. K. Tetrahedron Lett. 2000, 41, 1271.
27. (b) Yadav, J. S.; Reddy, B. V. S.; Raman, J. V.; Niranjan, N.; Kumar, S. K.; Kunwar, A. C. Tetrahedron Lett. 2002, 43, 2095.
28. (c) Das, S. K.; Reddy, K. A.; Abbineni, C.; Roy, J.; Rao, K. V. L. N.; Sachwani, R. H.; Iqbal, J. Tetrahedron Lett. 2003, 44, 4057.
29. (d) Das, S. K.; Reddy, K. A.; Roy, J. Synlett 2003, 1607.
30. (a) Yadav, J. S.; Reddy, B. V. S. Synthesis 2002, 511.
31. (b) Yadav, J. S.; Reddy, B. V. S.; Raju, A. K.; Rao, C. V. Tetrahedron Lett. 2002, 43, 5437.
32. (a) Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.; Kumar, G. M. Synlett 2000, 1450.
33. (b) Yadav, J. S.; Reddy, B. V. S.; Chand, P. K. Tetrahedron Lett. 2001, 42, 4057.
34. (c) Yadav, J. S.; Reddy, B. V. S.; Geetha, V. Synth. Commun. 2003, 33, 717.
35. (a) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 4053.
36. (b) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Synlett 2001, 427.
37. Yadav, J. S.; Reddy, B. V. S.; Reddy, J. S. S. J. Chem. Soc., Perkin Trans. 1 2002, 2390.
38. Yadav, J. S.; Reddy, B. V. S.; Rao, C. V.; Chand, P. K.; Prasad, A. R. Synlett 2001, 1638.
39. Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511.
40. Swamy, R. N.; Venkateshwarlu, A. Synthesis 2002, 598.
41. Bettadaiah, B. K.; Srinivas, P. Tetrahedron Lett. 2003, 44, 7257.
42. (a) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Satyanarayana, M. Tetrahedron Lett. 2002, 43, 7009.
43. (b) Danishefsky, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 3803.
44. (c) Babu, B. S.; Balasubramanian, K. K. Carbohydr. Lett. 1999, 3, 339.
45. (a) Reddy, Ch. S.; Smitha, G.; Chandrasekhar, S. Tetrahedron Lett. 2003, 44, 4693.
46. (b) Smitha, G.; Reddy, Ch. S. Tetrahedron 2003, 59, 9571.