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Synthesis of 20S-Protopanaxatriol β-D-Glucopyranosides

Author:
Atopkina, L. N., Denisenko, V. A.
Source:
Chemistry of natural compounds 2019 v.55 no.1 pp. 82-87
ISSN:
0009-3130
Subject:
Panax ginseng, Panax japonicus, chemistry, leaves, methylene chloride, organobromine compounds, sodium
Abstract:
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.
Agid:
6332316