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Glycosylation of triterpenoids of the dammarane series. VII. Dammar-24-ene-3α,12β,17α,20(S)-tetraol β-D-glucopyranosides

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Abstract

Glucosides have been synthesized from dammar-24-ene-3α,12β,17α,20(S)-tetraol (betulafolienetetraol), isolated from the leaves ofBetula pendula. Condensation with α-acetobromoglucose in the presence of silver oxide and silicate has given acetylated betulafolienetetraol 3- and 12- mono- and 3,12- and 3,20-di-O-β-D-glucopyranosides, the total yield of which amounted to 75–80%. The structures of the semisynthetic glycosides have been established on the basis of the results of IR,1H and13C NMR spectroscopy.

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Literature cited

  1. 1.

    N. D. Pokhilo, V. A. Denisenko, V. V. Makhan'kov, and N. I. Uvarova, Khim. Prir. Soedin., 179 (1986).

  2. 2.

    F. G. Fischer and N. Seiler, Ann. Che.,626, p. 185 (1959).

  3. 3.

    Y. Takemoto, T. Ueyama, H. Saito, S. Horio, S. Sanada, J. Shoji, S. Yahara, O. Tanaka, and S. Shibata, Chem. Pharm. Bull.,32, No. 8, p. 3128.

  4. 4.

    L. N. Atopkina, V. A. Denisenko, V. L. Novikov, and N. I. Uvarova, Khim. Prir. Soedin., 301 (1986).

  5. 5.

    H. Paulsen, and O. Lockhoff, Chem. Ber.,114, p. 3102 (1981).

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Additional information

Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 225–229, March–April, 1988.

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Atopkina, L.N., Samoshina, N.F., Denisenko, V.A. et al. Glycosylation of triterpenoids of the dammarane series. VII. Dammar-24-ene-3α,12β,17α,20(S)-tetraol β-D-glucopyranosides. Chem Nat Compd 24, 190–193 (1988). https://doi.org/10.1007/BF00596748

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Keywords

  • Oxide
  • Silicate
  • Organic Chemistry
  • Glycoside
  • Total Yield