Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-2-acetamido-2-deoxy-beta-D-glucopyranoside.
Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors.
Sun
Jiansong
J
State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, PR China.
Han
Xiuwen
X
Yu
Biao
B
D000045:Acacia / Q000737:chemistry; D031289:Albizzia / Q000737:chemistry; D002855:Chromatography, Thin Layer; D015394:Molecular Structure; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry*
D012503:Saponins; C480087:oleanolic acid 3-yl arabinopyranosyl-1-2-arabinopyranosyl-1-6-2-acetamido-2-deoxyglucopyranoside