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Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus

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Abstract

A method for preparative production of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT8 was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (3) under Koenigs—Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D-glucopyranoside if equimolar amounts of (2) and (3) were used.

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far-East Division, Russian Academy of Sciences, 690022, Vladivostok

    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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Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–48, January–February, 2006.

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Atopkina, L.N., Denisenko, V.A. Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus . Chem Nat Compd 42, 55–60 (2006). https://doi.org/10.1007/s10600-006-0035-4

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  • DOI: https://doi.org/10.1007/s10600-006-0035-4

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