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Glycosylation of 6α,12β-dihydroxy-20R,25-epoxydammaran-3-one

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Glycosylation of 6α,12β-dihydroxy-20R,25-epoxydammaran-3-one (panaxatriol 3-ketone, 2) under Koenigs–Knorr reaction conditions and the Helferich modification was studied. Condensation of 2 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (5) in the presence of Ag2O and 4-Å molecular sieves in CH2Cl2 gave acetylated 6α,12β-dihydroxy-20R,25-epoxydammaran-3-one 12-O-β-D-glucopyranoside whereas in the presence of Hg(CN)2 in nitromethane at 25°C the tetrahydropyran ring opened and, depending on the ratio of reagents, acetylated 12-, 12,25-di-, or 6,12,25-tri-O-β-D-glucopyranosides of 6α,12β,25-trihydroxydammar-20(22)E-en-3-one formed. 6α,12β-Dihydroxy-20R,25-epoxydammaran-3-one 12-O-β-D-glucopyranoside and 12-, 12,25-di-, and 6,12,25-tri-O-β-D-glucopyranosides of 6α,12β,25-trihydroxydammar-20(22)E-en-3-one were synthesized for the first time.

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Acknowledgment

The work was supported financially in part by the Interdisciplinary Integrated Project for Basic Research of the Siberian, Far-East, and Ural Branches, RAS (No. 12-II-SU-05-006).

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  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch, Russian Academy of Sciences, 690022, Vladivostok, Prosp. 100 Let Vladivostoku, 159, 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. 5, September–October, 2014, pp. 751–757.

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Atopkina, L.N., Denisenko, V.A. Glycosylation of 6α,12β-dihydroxy-20R,25-epoxydammaran-3-one. Chem Nat Compd 50, 868–875 (2014). https://doi.org/10.1007/s10600-014-1103-9

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  • DOI: https://doi.org/10.1007/s10600-014-1103-9

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