The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides.
Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described.
Zou
Chuan-Chun
CC
Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China.
Hou
Shu-Jie
SJ
Shi
Yang
Y
Lei
Ping-Sheng
PS
Liang
Xiao-Tian
XT
D000107:Acetylation; D002236:Carbohydrate Conformation; D004144:Diosgenin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D019791:Guanidine / Q000737:chemistry; D012503:Saponins / Q000138:chemical synthesis; D013150:Spirostans / Q000138:chemical synthesis*
D012503:Saponins; D013150:Spirostans; C044934:gracillin; C019357:dioscin; D019791:Guanidine; D004144:Diosgenin