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Novel optically active 1,3-aminoalcohols derived from D-glucal

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A series of ethyl(phenyl) 6-amino-2,3,6-trideoxy-α-D-glucopyranosides (amino=piperidino (Pip), pyrrolidino (Pyr), azetidino (Az), Bu2N) have been prepared from tri-O-acetyl-D-glucal to obtain catalysts for asymmetric synthesis and the starting compounds for the syntheses of other bidentate ligands.

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References

  1. J. Seyden-Penne,Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 716 (1995).

    Google Scholar 

  2. R. Noyori,Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 378 (1994).

    Google Scholar 

  3. Catalytic Asymmetric Synthesis, I. Ojima (ed.), VCH, New York, 476 (1993).

    Google Scholar 

  4. Houben-Weyl,Methods of Organic Chemistry, E21a-E21f.Stereoselective Synthesis, eds: G. Helmchen, R. W. Hoffman, J. Mulzer, and E. Schaumann, Thieme, Stuttgart, New York (1995).

    Google Scholar 

  5. D. J. Ager, I. Prakash, and D. R. Schaad,Chem. Rev.,92, 835 (1996).

    Article  Google Scholar 

  6. A. Vidal-Ferran, A. Moyano, M. A. Perricas, and A. Riera,J. Org. Chem.,62, 4970 (1997).

    Article  Google Scholar 

  7. F. W. Lichtenthaler,Carbohydrates — Synthetic Methods and Applications in Medicinal Chemistry, eds. H. Ogura, A. Hasegawa, and T. Suami, Kodansha, Tokyo, VCH, New York, 3 (1992).

    Google Scholar 

  8. H. Brunner and W. Pieronzyk,J. Chem. Res. Synop., 74 (1980).

  9. M. Yamashita, M. Kobayashi, M. Siguira, K. Tsunokawa, T. Oshikawa, S. Inokawa, and H. Yamamoto,Bull. Chem. Soc. Jpn.,59, 175 (1986).

    Google Scholar 

  10. I. Habus, Z. Raza, and V. Sunjic,J. Mol. Catal.,42, 173 (1987).

    Article  Google Scholar 

  11. R. Selke and H. Praceus,J. Mol. Catal.,37, 213 (1986).

    Article  Google Scholar 

  12. R. Selke, M. Schwarze, H. Baudisch, I. Grassert, M. Michalic, G. Oehme, N. Stoll, and B. Costisella,J. Mol. Catal.,84, 213 (1993).

    Google Scholar 

  13. G. Oehme, I. Iovel, Ch. Facklam, and E. Lukevics,Chem. Heterocycl. Comp.,31, 735 (1995).

    Google Scholar 

  14. I. Iovel, K. Rubina, J. Popelis, A. Gaukhman, and E. Lukevics,Chem. Heterocycl. Comp.,32, 294 (1996).

    Article  Google Scholar 

  15. I. Iovel, J. Popelis, M. Fleisher, and E. Lukevics,Tetrahedron: Asymmetry,7, 1279 (1997).

    Article  Google Scholar 

  16. I. Iovel, G. Oehme, and E. Lukevics,Appl. Organomet. Chem.,12, 469 (1998).

    Article  Google Scholar 

  17. G. Oehme, I. Iovel, and E. Lukevics,Appl. Organomet. Chem.,13, 481 (1999).

    Article  Google Scholar 

  18. H. Paulsen,Angew. Chem. Intern. Ed. Eng.,21, 155 (1982).

    Article  Google Scholar 

  19. N. L. Holder,Chem. Rev.,82, 287 (1982).

    Article  Google Scholar 

  20. B. Fraser-Reid,Acc. Chem. Res.,18, 347 (1985).

    Article  Google Scholar 

  21. R. J. Ferrier, W. G. Overend, and A. E. Ryan.J. Chem. Soc., 3667 (1962).

  22. R. J. Ferrier,J. Chem. Soc., 5443 (1964).

  23. R. J. Ferrier and G. H. Sankey,J. Chem. Soc. (C), 2339 (1966).

  24. R. J. Ferrier and N. J. Prasad.J. Chem. Soc. (C), 570 (1969).

  25. R. J. Ferrier and N. Vethaviyasar,Carbohydr. Res.,13, 269 (1970).

    Article  Google Scholar 

  26. S. Laland, W. G. Overend, and M. Stacey,J. Chem. Soc., 738 (1950).

  27. A. B. Foster, R. Harrison, J. Lehmann, and J. M. Webber,J. Chem. Soc., 4471 (1963).

  28. K. R. Wood and P. W. Kent,J. Chem. Soc. (C), 2422 (1967).

  29. B. Fraser-Reid, S. Y.-K. Tam, and B. Radatus,Can. J. Chem.,53, 2005 (1975).

    Google Scholar 

  30. J. M. Berry and L. D. Hal,Carbohydr. Res.,47, 307 (1976).

    Article  Google Scholar 

  31. D. E. Iley and B. Fraser-Reid,Can. J. Chem.,57, 653 (1979).

    Google Scholar 

  32. G. Descotes, J.-C. Martin, D. Sinou, and T.-C. Dung,Bull. Soc. Chim. France, II-61 (1979).

  33. G. Grynkiewicz, W. Priebe, and A. Zanojski,Carbohydr. Res.,68, 33 (1979).

    Article  Google Scholar 

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 45–52, January, 2000.

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Iovel, I., Oehme, G., Michalik, M. et al. Novel optically active 1,3-aminoalcohols derived from D-glucal. Chem Heterocycl Compd 36, 40–46 (2000). https://doi.org/10.1007/BF02256842

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  • DOI: https://doi.org/10.1007/BF02256842

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