An improved synthesis of the saponin, polyphyllin D.
Polyphyllin D, namely diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)- [(alpha-L-arabinofuranosyl)-(1 --> 4)]-[beta-D-glucopyranoside, was synthesized from diosgenyl-beta-D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha-L-rhamnopyranosylation reactions.
Li
B
B
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, People's Republic of China.
Yu
B
B
Hui
Y
Y
Li
M
M
Han
X
X
Fung
K P
KP
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004144:Diosgenin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D012503:Saponins; D014312:Trisaccharides; C121203:polyphyllin D; D004144:Diosgenin