Chemistry of Natural Compounds

, Volume 25, Issue 6, pp 690–693 | Cite as

Glycosylation of triterpenoids of the dammarane series. X. Regio- and stereoselective synthesis of 20(S)-protopanaxadiol 3-O-β-D-glucopyranoside (ginsenoside Rh2)

  • L. N. Atopkina
  • N. F. Samoshina
  • N. I. Uvarova
Article

Abstract

The regio- and stereoselective synthesis of ginsenoside Rh2, which possesses antitumoral activity, has been effected by the glycosylation of 12β-acetoxydammar-24-ene-3β,20(S)-diol. Condensation with α-acetobromoglucose was carried out in the presence of silver oxide in dichloroethane at room temperature, and the yield of the desired glycoside amounted to 50%. A method for the selective protection of the C-12-OH group of dammar-24-ene-3β,12β,20(S)-triol [20(S)-protopanaxadiol] has been proposed.

Keywords

Ginsenoside Silver Oxide Triol Stereoselective Synthesis Sodium Tetrahydroborate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    K. Fujikawa-Yamamoto, T. Ota, S. Odashima, H. Abe, and S. Arichi, Cancer J.,1, No. 8, 349 (1987).Google Scholar
  2. 2.
    T. Ota, K. Fujikawa-Yamamoto, Z. Zong, M. Yamasaki, S. Odashima, I. Kitagawa, H. Abe, and S. Arichi, Cancer Res.,47, No. 14, 3863 (1987).PubMedGoogle Scholar
  3. 3.
    Japanese Patent No. 58 57, 399, Chem. Abstr.,99, 76852u (1983).Google Scholar
  4. 4.
    L. N. Atopkina, V. A. Denisenko, N. I. Uvarova, and G. B. Elyakov, Carbohydr. Res.,177, 101 (1988).CrossRefGoogle Scholar
  5. 5.
    F. G. Fischer and N. Seiler, Ann. Chem.,626, 185 (1959).Google Scholar
  6. 6.
    M. Nagai, N. Tanaka, O. Tanaka, and S. Ishikawa, Chem. Pharm. Bull.,9, 2061 (1973).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • L. N. Atopkina
  • N. F. Samoshina
  • N. I. Uvarova

There are no affiliations available

Personalised recommendations