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

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 C...

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Bibliographic Details
Published in:Chemistry of natural compounds 2014, Vol.50 (5), p.868-875
Main Authors: Atopkina, L. N, Denisenko, V. A
Format: Article
Language:English
Subjects:
chemical structure
glucosides
glycosylation
ketones
Medicine
Organic Chemistry
organobromine compounds
Pharmacy
Plant Sciences
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Summary: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.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-014-1103-9