Highly stereoselective synthesis of 1,2-trans-glycosides using p-chlorobenzylated glycosyl carbonate as glycosyl donor

Chemistry Letters

Volumn , Issue 7, 1998, Pages 635-636

  Mukaiyama, Teruaki ^a   Miyazaki, Kazuo ^a   Uchiro, Hiromi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032398319     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.635     Document Type: Article

References (21)

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9. S. Hashimoto, M. Hayashi, and R. Noyori, Tetrhedron. Lett., 25, 1379 (1984); S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; R. R. Schmidt, M. Behrendt, and A. Toepfer, Synlett, 1990, 694; Y. D. Vankar, P. S. Vankar, M. Behrendt, and R. R. Schmidt, Tetrahedron, 47, 9985 (1991); K. Koide, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 32, 7065 (1992); H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, and C. H. Wong, J. Org. Chem., 59, 864(1994); S. Hashimoto, K. Umeo, A. Sano, N. Watanabe, M. Nakajima, and S. Ikegami, Tetrahedron Lett., 36, 2251(1995); K. Fukase, I. Kinoshita, T. Kanoh, Y. Nakai, A. Hasuoka, and S. Kusumoto, Tetrahedron, 52, 3897 (1996).
10. S. Hashimoto, M. Hayashi, and R. Noyori, Tetrhedron. Lett., 25, 1379 (1984); S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; R. R. Schmidt, M. Behrendt, and A. Toepfer, Synlett, 1990, 694; Y. D. Vankar, P. S. Vankar, M. Behrendt, and R. R. Schmidt, Tetrahedron, 47, 9985 (1991); K. Koide, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 32, 7065 (1992); H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, and C. H. Wong, J. Org. Chem., 59, 864(1994); S. Hashimoto, K. Umeo, A. Sano, N. Watanabe, M. Nakajima, and S. Ikegami, Tetrahedron Lett., 36, 2251(1995); K. Fukase, I. Kinoshita, T. Kanoh, Y. Nakai, A. Hasuoka, and S. Kusumoto, Tetrahedron, 52, 3897 (1996).
11. S. Hashimoto, M. Hayashi, and R. Noyori, Tetrhedron. Lett., 25, 1379 (1984); S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; R. R. Schmidt, M. Behrendt, and A. Toepfer, Synlett, 1990, 694; Y. D. Vankar, P. S. Vankar, M. Behrendt, and R. R. Schmidt, Tetrahedron, 47, 9985 (1991); K. Koide, M. Ohno, and S. Kobayashi, Tetrahedron Lett., 32, 7065 (1992); H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, and C. H. Wong, J. Org. Chem., 59, 864(1994); S. Hashimoto, K. Umeo, A. Sano, N. Watanabe, M. Nakajima, and S. Ikegami, Tetrahedron Lett., 36, 2251(1995); K. Fukase, I. Kinoshita, T. Kanoh, Y. Nakai, A. Hasuoka, and S. Kusumoto, Tetrahedron, 52, 3897 (1996).
12. H. Uchiro and T. Mukaiyama, Chem. Lett., 1996, 271; H. Uchiro, K. Miyazaki, and T. Mukaiyama, Chem. Lett., 1997, 403.
13. H. Uchiro and T. Mukaiyama, Chem. Lett., 1996, 271; H. Uchiro, K. Miyazaki, and T. Mukaiyama, Chem. Lett., 1997, 403.
14. Quite recently, oligosaccharide synthesis utilizing chemical stability of p-chlorobenzylated glycoside under the acidic condition was reported: N. L. Pohl and L. L. Kiessling, Tetrahedron Lett., 40, 6985(1997).
15. H. Uchiro and T. Mukaiyama, Chem. Lett. 1997, 121.
16. 9
17. S. Koto, S. Inada, N. Morishima, and S. Zen, Carbohydr. Res., 87, 294(1980).
18. M. Bols and H. C. Hansen, Acta Chem. Scand., 47, 818 (1993).
19. Since the melting point of pivalonitrile is 15°C, a mixed solvent was applied to the reaction at lower temperature.
20. Examples of glycosylation utilizing phenylcarbonate-type glycosyl donors have been reported: R. Ishido, I. Takai, and K. Shibasaki, Japanese Patent, JP 9409674(1994); T. Mukaiyama, T. Sasaki, E. Iwashita, and K. Matsubara, Chem. Lett. 1995, 455.
21. Examples of glycosylation utilizing phenylcarbonate-type glycosyl donors have been reported: R. Ishido, I. Takai, and K. Shibasaki, Japanese Patent, JP 9409674(1994); T. Mukaiyama, T. Sasaki, E. Iwashita, and K. Matsubara, Chem. Lett. 1995, 455.