Glycosyl fluoride for glycosidation promoted by a catalytic amount of gallium reagent

Synthesis

Volumn , Issue 10, 1996, Pages 1175-1176

  Koide, Kazunori ^a   Ohno, Masaji ^a,c   Kobayashi, Susumu ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c EISAI CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; CATALYSIS; GLYCOSYLATION; REACTION ANALYSIS;

EID: 0029853281     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4363     Document Type: Article

References (13)

1. Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431-432.
2. Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382.
3. Matsumoto, T.; Maeta, H.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1988, 29, 3567-3570. Suzuki, K.; Maeta, H.; Matsumoto, T.; Tsuchihashi, G. Tetrahedron Lett. 1988, 29, 3571-3574.
4. Matsumoto, T.; Maeta, H.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1988, 29, 3567-3570. Suzuki, K.; Maeta, H.; Matsumoto, T.; Tsuchihashi, G. Tetrahedron Lett. 1988, 29, 3571-3574.
5. In Lange's Handbook of Chemistry, Dean, J.A.; Ed.; Mc-Graw-Hill, Inc.: New York, 1973; p 3-125.
6. Kobayashi, S.; Koide, K.; Ohno, M. Tetrahedron Lett. 1990, 31, 2435-2438.
7. Purchased from Trichemical Co., Ltd., Japan.
8. Eisch, J.J. J. Am. Chem. Soc. 1962, 84, 3830-3836. Tuck, D.G. Gallium and Indium. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F.G.A.; Abel, E.W. Eds.; Pergamon: Oxford, 1982; Vol 1, pp. 683-723.
9. Eisch, J.J. J. Am. Chem. Soc. 1962, 84, 3830-3836. Tuck, D.G. Gallium and Indium. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F.G.A.; Abel, E.W. Eds.; Pergamon: Oxford, 1982; Vol 1, pp. 683-723.
10. When free alcohol was employed as a glycosyl acceptor instead of TMS ether, the glycosidation reaction proceeded very slowly. Therefore, the corresponding TMS ether was used in the present study.
11. f = 0.48 (EtOAc/Hexane = 1/6).
12. 2GaOTf (10 mol%) affording the corresponding aldol in quantitative yields: Koide, K.; Kobayashi, S. unpublished results.
13. Koide, K.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1991, 32, 7065-7068.