A mild, efficient and α-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 13, 2004, Pages 3611-3614

  Rafiee, Ezzat ^a   Tangestaninejad, Shahram ^a   Habibi, Mohammad H ^a   Mirkhani, Valiollah ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Ferrier rearrangement; Glucal; Glycosidation; Polyoxometalate

Indexed keywords

ALCOHOL DERIVATIVE; GLYCOPYRANOSIDE; GLYCOSIDE; METAL; PHENOL DERIVATIVE; POTASSIUM DODECATUNGSTOCOBALTATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; ELECTRON TRANSPORT; ENVIRONMENTAL TEMPERATURE; GLYCOSIDATION; SYNTHESIS;

BENZYL ALCOHOL; CATALYSIS; COBALT; GLYCOSIDES; GLYCOSYLATION; MODELS, CHEMICAL; PHENOLS; POTASSIUM; SOLVENTS; TUNGSTEN COMPOUNDS;

EID: 2942585504     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.110     Document Type: Article

References (39)

1. Williams N.R., Wander J.D. The Carbohydrates Chemistry and Biochemistry. 1980;Academic, New York. p 761
2. Fraser-Reid B. Acc. Chem. Res. 18:1985;347
3. Ferrier R.J. Adv. Carbohydr. Chem. Biochem. 1969;199
4. Ramnauth J., Poulin O., Rakhit S.P., Maddaford S.P. Org. Lett. 3:2001;2013
5. Collins P., Ferrier R. Monosaccharides: their Chemistry and their Roles in Natural Products. 1995;Wiley, Chichester
6. Ferrier R.J., Prasad N. J. Chem. Soc. C. 1969;570
7. Descots G., Martin J.C. Carbohydr. Res. 56:1977;168
8. Grynkiewicz G., Priebe W., Zamojski A. Carbohydr. Res. 68:1979;33
9. Casiraghi G., Cornia M., Russu G., Zetta L., Facca G.G., Belicchi M.F. Tetrahedron Lett. 29:1988;3323
10. Postema M.H.D. Tetrahedron. 40:1992;8545
11. Toshima K., Tatsuta K. Chem. Rev. 93:1993;1503
12. Levy D.E., Tang C. The Chemistry of C-Glycosides. 1995;Pergamon, New York
13. Klaffke P., Pudlo, Springer D., Thiem J. Liebigs Ann. Chem. 1991;509
14. Grynkiewicz G., Priebe A., Zamojski A. Carbohydr. Res. 68:1979;33
15. Bhate P., Horton D., Priebe W. Carbohydr. Res. 144:1985;331
16. Toshima K., Ishizuka T., Matsuo G., Nakata M. Synlett. 1995;306
17. Toshima K., Miyamoto N., Matsuo G., Kakata M., Matsumura S. Chem. Commun. 1996;1379
18. Toshima K., Ishizuka T., Matsuo G., Nakata M., Konoshita M. J. Chem. Soc., Chem. Commun. 1993;704
19. Toshima K., Ishizuka T., Matsuo G., Nakata M. Chem. Lett. 1993;2013
20. Swamy N.R., Venkateswarlu Y. Synthesis. 5:2002;598
21. Fraser-Reid B., Madsen R. J. Org. Chem. 60:1995;3851
22. López J.C., Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1992;94
23. Babu B.B., Balasubramanian K.K. Tetrahedron Lett. 41:2000;1271
24. For some reviews on O-glycosidations, see: Schmidt R.R. Angew. Chem., Int. Ed. Engl. 25:1986;212
25. Sinaÿ P. Pure Appl. Chem. 63:1991;519
26. Boons G.J. Tetrahedron. 52:1996;1095
27. Weinstock I.A. Chem. Rev. 98:1998;113
28. Chester A.W. J. Org. Chem. 35:1970;1797
29. Eberson L. J. Am. Chem. Soc. 105:1983;3192
30. Balocchi E., Bietti M., Mattioli M. J. Org. Chem. 58:1993;7106
31. Habibi M.H., Tangestaninejad S., Mohammadpoor-Baltork I., Mirkhani V., Yadollahi B. Tetrahedron Lett. 42:2001;2851
32. Habibi M.H., Tangestaninejad S., Mirkhani V., Yadollahi B. Tetrahedron. 57:2001;8333
33. Marzabadi C.H., Franck R.W. Tetrahedron. 56:2000;8385
34. Kirby A.J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. 1983;Springer, New York
35. Deslong-champs P. Stereoelectronic Effects in Organic Chemistry. 1983;Pergamon, Oxford
36. Thiem J., Klaffke W. Top. Curr. Chem. 154:1990;285
37. Iranpoor N., Baltork I.M. Tetrahedron Lett. 31:1990;735
38. Tanemura T., Suzuki T., Hoaguchi T. J. Chem. Soc., Perkin Trans. 1. 1992;2997
39. Roush W., Sebesta P.D., James R.A. Tetrahedron. 53:1997;8837