Glycosylation of sialyl acetates with a novel catalyst combination: Bismuth triflate and BF3·OEt2 system

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 14, 2003, Pages 3073-3076

  Ikeda, Kiyoshi ^a   Torisawa, Yasuhiro ^b   Nishi, Takao ^b   Minamikawa, Junichi ^b   Tanaka, Kiyoshi ^a   Sato, Masayuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZYL ALCOHOL; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; BISMUTH DERIVATIVE; BISMUTH TRIFLATE; BORON DERIVATIVE; BORON TRIFLUORIDE ETHERATE; CARBOHYDRATE DERIVATIVE; DICHLOROMETHANE; HYDROGEN; METAL; N ACETYLNEURAMINIC ACID DERIVATIVE; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; DIELS ALDER REACTION; GLYCOSYLATION; PURIFICATION; ROOM TEMPERATURE;

EID: 0037785466     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00277-3     Document Type: Article

References (24)

1. Rosenberg A. Biology of Sialic Acids. 1995;Plenum, New York, London.
2. Boons G.-J., Demchenko A.V. Chem. Rev. 100:2000;4539.
3. (a) Toshima K., Tatsuta K. Chem. Rev. 93:1993;1503
4. (b) Kobayashi S., Sugiura M., Kitagawa H., Lam W.W.-L. Chem. Rev. 102:2002;2227.
5. Komatsu, N. In Organobithmuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier, Amsterdam, 2001, Chapter 5, p 371.
6. (a) Labrouillere M., Le Roux C., Gaspard H., Laporterie A., Dubac J. Tetrahedron Lett. 40:1999;285.
7. (b) Torisawa Y., Nishi T., Minamikawa J. Org. Process Res. Dev. 5:2001;84
8. (c) Repichet S., Zwick A., Vendier A.L., LeRoux C., Dubac J. Tetrahedron Lett. 43:2002;993. and references therein.
9. Repichet S., Le Roux C., Dubac J., Desmurs J.-R. Eur. J. Org. Chem. 1998;2743.
10. Repichet S., Le Roux C., Hernandez P., Dubac J. J. Org. Chem. 64:1999;6479.
11. Garrigues B., Gonzaga F., Robert H., Dubac J. J. Org. Chem. 62:1997;4880.
12. Laurent-Robert H., Garrigues B., Dubac J. Synlett. 2000;1160.
13. Laurent-Robert H., Le Roux C., Dubac J. Synlett. 1998;1138.
14. Orita A., Tanahashi C., Kakuda A., Otera J. Angew. Chem., Int. Ed. 39:2000;2877.
15. Hashizume N., Kobayashi S. Carbohydr. Lett. 2:1996;157.
16. Yamada K., Fujita E., Nishimura S.-I. Carbohydr. Res. 305:1998;443.
17. (a) Yamanoi T., Iwai T., Inazu T. J. Carbohydr. Chem. 4&5:1998;819.
18. (b) Yamanoi T., Iwai T., Inazu T. Heterocycles. 53:2000;1263.
19. Roos G.H.P., Rampersadh P. Synth. Commun. 23:1993;1261.
20. (a) Torisawa Y., Nishi T., Minamikawa J. Bioorg. Med. Chem. Lett. 12:2002;387
21. (b) Torisawa, Y.; Nishi, T.; Minamikawa, J. Bioorg. Med. Chem. 2003, 11, 2205.
22. Higashi K., Miyoshi S., Nakabayashi S., Yamada H., Ito Y. Chem. Pharm. Bull. 40:1992;2300.
23. Martin T.J., Brescello R., Toepfer A., Schmidt R.R. Glycoconjugate J. 10:1993;16.
24. Dabrowski U., Friebolin H., Brossmer R., Supp M. Tetrahedron Lett. 20:1979;4637.