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Synthesis of acetylated glycosides of hydroxynaphthoquinones

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Chemistry of Natural Compounds Aims and scope

Abstract

A method is proposed for the synthesis of acetylated glycosides of hydroxynaphthoquinones. The condensation of D-glucose and D-galactose (tert-butyl orthoacetate)s with lawsone and lapachol has given the tetra-O-acetyl-β-D-glucopyranosides of lawsone and of lapachol and the tetra-O-acetyl-β-galactopyranoside of lawsone. The structures of the glycosides obtained have been confirmed by IR and1H and13C NMR spectroscopy. The structure of the lawsone acetylgalactopyranoside described previously has been corrected.

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Literature cited

  1. P. N. Cote and L. Goodman, Carbohydr. Res.,26, 247 (1973).

    Google Scholar 

  2. M. C. F. Linardi, M. M. de Oliveira, and M. R. P. Sampaio, J. Med. Chem.,18, 1159 (1975).

    Google Scholar 

  3. M. M. de Oliveira, M. C. F. Linardi, and M. R. P. Sampaio, J. Pharm. Sci.,67, 562 (1978).

    Google Scholar 

  4. N. Steinerova, J. Cudlin, and Z. Vanek, Collect. Czech. Chem. Commun.,45, 2684 (1980).

    Google Scholar 

  5. N. K. Kochetkov and A. F. Bochkov, in: Recent Developments in the Chemistry of Natural Compounds, Akademiii Kiado, Budapest (1971).

    Google Scholar 

  6. K. Honma and A. Hamada, Chem. Pharm. Bull. (Tokyo),24, 1165 (1976).

    Google Scholar 

  7. S. G. Polonik, A. M. Tolkach, and N. I. Uvarova, Inventor's Certificate No. 892,899; Byull. Izobret., No. 37, 271 (1982).

  8. A. F. Bochkov, V. A. Afanas'ev, and G. E. Zaikov, The Formation and Cleavage of Glycosidic Bonds [in Russian], Moscow (1978), p. 37.

  9. L. Fieser and M. Fieser, Organic Chemistry, 3rd edn., Reinhold, New York (1956).

    Google Scholar 

  10. I. A. McDonald, T. J. Simpson, and A. F. Sierakovski, Aust. J. Chem.,30, 1727 (1977).

    Google Scholar 

  11. D. Y. Gagnaire, F. R. Taravel, and M. R. Vignon, Carbohydr. Res.,51, 157 (1976).

    Google Scholar 

  12. N. Donaldson, The Chemistry and Technology of Naphthalene Compounds, Arnold, London (1958).

    Google Scholar 

  13. N. Jacobsen and K. Torrssel, Acta. Chim. Scand.,27, 3211 (1973).

    Google Scholar 

  14. N. K. Kochetkov and S. F. Bochkov, in: Methods of Investigating Carbohydrates [in Russian], Moscow (1975), p. 302.

  15. A. I. Bashkatova, G. V. Smirnova, V. I. Volynskaya, I. Shvets, and R. P. Evstigneeva, Zh. Org. Khim.,9, 1393 (1973).

    Google Scholar 

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Authors
  1. S. G. Polonik
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  2. A. M. Tolkach
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  3. N. I. Uvarova
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Additional information

Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 324–327, May–June, 1983.

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Polonik, S.G., Tolkach, A.M. & Uvarova, N.I. Synthesis of acetylated glycosides of hydroxynaphthoquinones. Chem Nat Compd 19, 307–310 (1983). https://doi.org/10.1007/BF00579766

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  • DOI: https://doi.org/10.1007/BF00579766

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