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Synthesis of 20S-Protopanaxatriol β-D-Glucopyranosides

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Chemistry of Natural Compounds Aims and scope

Condensation of 20S-protopanaxatriol (3β,6α,12β,20S-tetrahydroxydammar-24-ene) (1) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) in the presence of Ag2O in CH2Cl2 gave a mixture of acetylated 3-, 12-, 20-, 3,12-di-, and 3,20-di-O-β-D-glucopyranosides 3–7 that was dominated by 3-O-β-Dglucopyranoside tetraacetate 3 (47%). Subsequent deacetylation by sodium methoxide produced free β-D-glucopyranosides 8–12, three of which were identical to chikusetsusaponin-L10, ginsenoside-F1, and ginsenoside-Ia, which were isolated earlier from leaves of Panax japonicus and P. ginseng. 3-Mono- and 3,12-di-O-β-D-glucopyranosides 8 and 11 were prepared for the first time.

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Acknowledgment

We thank the Korea Ginseng & Tobacco Research Institute (now Korean Ginseng Corp., Central Research Institute, Daejeon, Korea) for supplying 20S-protopanaxatriol.

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, 159 Prosp. 100 Let Vladivostoku, Vladivostok, 690022, Russia

    L. N. Atopkina & V. A. Denisenko

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  1. L. N. Atopkina
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  2. V. A. Denisenko
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Correspondence to L. N. Atopkina.

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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2019, pp. 71–75.

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Atopkina, L.N., Denisenko, V.A. Synthesis of 20S-Protopanaxatriol β-D-Glucopyranosides. Chem Nat Compd 55, 82–87 (2019). https://doi.org/10.1007/s10600-019-02618-6

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  • DOI: https://doi.org/10.1007/s10600-019-02618-6

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