Synthesis of ginsenoside Rg3, a minor constituent of Ginseng radix.
Glycosylation of 12beta-acetoxy-dammar-24-en-3beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha- and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg3, the minor component of Ginseng Radix rubra. All compounds were fully characterized by 1H and 13C NMR spectroscopy.
Anufriev
V P
VP
Laboratory of Organic Synthesis of Natural Products, Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok.
Malinovskaya
G V
GV
Denisenko
V A
VA
Uvaròva
N I
NI
Elyakov
G B
GB
Kim
S I
SI
Baek
N I
NI
D000107:Acetylation; D036145:Ginsenosides; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D005894:Panax / Q000737:chemistry*; D010946:Plants, Medicinal; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
D036145:Ginsenosides; D012503:Saponins; C097367:ginsenoside Rg3