title: The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides.
abstract: 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.
authors.affiliation: Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China.
authors.forename: Chuan-Chun
authors.initials: CC
authors.lastname: Zou
authors.forename: Shu-Jie
authors.initials: SJ
authors.lastname: Hou
authors.forename: Yang
authors.initials: Y
authors.lastname: Shi
authors.forename: Ping-Sheng
authors.initials: PS
authors.lastname: Lei
authors.forename: Xiao-Tian
authors.initials: XT
authors.lastname: Liang
mesh_terms: 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*
chemical_list: D012503:Saponins; D013150:Spirostans; C044934:gracillin; C019357:dioscin; D019791:Guanidine; D004144:Diosgenin