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Triterpenoid saponins

13. Halolysis of glycosides of the triterpene series and the synthesis of glucosides of oleanolic acid

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    By the condensation of acetobromoglucose with methyl oleanolate in presence of mercuric acetate and with 3-O-acetyloleanolic acid in presence of silver carbonate methyl oleanolate α-D-glucoside and 1-(3-O-acetyl-oleanoloyl)-β-D-glucopyranose were obtained, respectively.

  2. 2.

    By the halolysis of methyl oleanolate α- andβ -glucosides with lithium iodide in collidine, oleanolic acid 3-O-α- and 3-O-β -glucosides were obtained, respectively, which indicates the stability of a glycoside link of the usual type under the conditions of the halolysis reaction.

  3. 3.

    With 1-(3-O-acetyloleanoloyl)-β -D-glucose and araloside A as examples, the possibility of the selective cleavage of the acyl glycoside link in halolysis was demonstrated.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 11, pp. 2028–2036, November, 1964

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Kochetkov, N.K., Khorlin, A.Y. & Snyatkova, V.I. Triterpenoid saponins. Russ Chem Bull 13, 1925–1931 (1964). https://doi.org/10.1007/BF00844489

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  • DOI: https://doi.org/10.1007/BF00844489

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