Catalytic stereoselective synthesis of α-D-galactopyranosides from 2,3,4,6-tetra-O-benzyl-D-galactopyranose and several alcoholic nucleophiles

Chemistry Letters

Volumn , Issue 5, 1997, Pages 403-404

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

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000241103     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.403     Document Type: Article

References (25)

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4. General review of O-glycosylation: K. Toshima and K. Tatsuta, Chem. Rev., 93, 1503(1993); K. Suzuki and T. Nagasawa, J. Synth. Org. Chem. Jpn., 50, 378(1992).
5. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
6. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
7. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
8. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
9. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
10. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
11. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
12. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
13. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
14. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
15. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
16. Stoichiometric reactions: N. Morishima, S. Koto, and S. Zen, Bull. Chem. Soc. Jpn., 52, 784 (1979); S. Koto, N. Morishima, and S. Zen. Bull. Chem. Soc. Jpn., 55, 1543(1982); S. Koto, N. Morishima, C. Kusuhara, S. Sekido, T. Yoshida, and S. Zen, Bull. Chem. Soc. Jpn., 55, 2995(1982); S. Koto, N. Morishima, M. Owa, and S. Zen, Carbohydr. Res., 130, 73(1984); B. Fischer, A. Nudelman, M. Ruse, J. Herzig, and H. E. Gottlieb, J. Org. Chem., 26, 4634(1984); T. Mukaiyama and S. Suda, Chem. Lett., 1990, 1143; S. Suda and T. Mukaiyama, Chem. Lett., 1991, 431; T. Mukaiyama, K. Matsubara, and S. Suda, Chem. Lett., 1991, 981; T. Mukaiyama and K. Matsubara, Chem. Lett., 1992, 1041; H. Susaki, Chem. Pharm. Bull., 42, 1917 (1994). Catalytic reactions: J. Inanaga, Y. Yokoyama, and T. Hanamoto, J. Chem. Soc., Chem. Commun., 1993, 1090; T. Mukaiyama and N. Shimomura, Chem. Lett., 1993, 781.
17. T. Mukaiyama, K. Matsubara, and M. Hora, Synthesis, 1994, 1368.
18. H. Uchiro and T. Mukaiyama, Chem. Lett., 1996, 79.
19. H. Uchiro and T. Mukaiyama, Chem. Lett., 1996, 271.
20. 2 And it was also observed that the use of Sn(OTf)2-Me3SiCl catalyst system was more effective compared with that of Me3SiOTf alone in the present glycosytation (Table 1, Entry 10).
21. Similar active species were assumed in the previously reported Me3SiCl-SnCl2 or TrCl-SnCl2 catalyzed C-C bond forming reactions, see N. Iwasawa and T. Mukaiyama, Chem. Lett., 1987, 463; T. Mukaiyama, S. Kobayashi, M. Tamura, and Y. Sagawa, Chem. Lett., 1987, 491.
22. Similar active species were assumed in the previously reported Me3SiCl-SnCl2 or TrCl-SnCl2 catalyzed C-C bond forming reactions, see N. Iwasawa and T. Mukaiyama, Chem. Lett., 1987, 463; T. Mukaiyama, S. Kobayashi, M. Tamura, and Y. Sagawa, Chem. Lett., 1987, 491.
23. Anomerization reactions of alkyl glycosides using several Lewis acids were reported: S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, and S. Zen, Bull. Chem. Soc. Jpn., 55, 1092(1982); N. Ikemoto, O. K. Kim, L-C. Lo, V. Satyanarayana, M. Chang, and K. Nakanishi, Tetrahedron Lett., 30, 4295(1992); C. K. Lee, E. J. Kim, and I-S. H. Lee, Carbohydr. Res., 240, 197(1993).
24. Anomerization reactions of alkyl glycosides using several Lewis acids were reported: S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, and S. Zen, Bull. Chem. Soc. Jpn., 55, 1092(1982); N. Ikemoto, O. K. Kim, L-C. Lo, V. Satyanarayana, M. Chang, and K. Nakanishi, Tetrahedron Lett., 30, 4295(1992); C. K. Lee, E. J. Kim, and I-S. H. Lee, Carbohydr. Res., 240, 197(1993).
25. Anomerization reactions of alkyl glycosides using several Lewis acids were reported: S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, and S. Zen, Bull. Chem. Soc. Jpn., 55, 1092(1982); N. Ikemoto, O. K. Kim, L-C. Lo, V. Satyanarayana, M. Chang, and K. Nakanishi, Tetrahedron Lett., 30, 4295(1992); C. K. Lee, E. J. Kim, and I-S. H. Lee, Carbohydr. Res., 240, 197(1993).