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Chemistry of Natural Compounds

, Volume 42, Issue 1, pp 55–60 | Cite as

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

  • L. N. Atopkina
  • V. A. Denisenko
Article

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.

Key words

dammarane triterpenoids 12-keto-20S-protopanaxadiol 3β-20S-dihydroxydammar-24-en-12-one chikusetsusaponin-LT8 Betula Panax japonicus 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • L. N. Atopkina
    • 1
  • V. A. Denisenko
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far-East DivisionRussian Academy of SciencesVladivostok

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