Facile sythesis of dioscin and its analogues

被引:16
作者
Hou, SJ
Zou, CC
Zhou, L
Lei, PS [1 ]
Yu, DQ
机构
[1] Peking Union Med Coll, Inst Mat Med, Beijing 100050, Peoples R China
[2] Chinese Acad Med Sci, Beijing 100050, Peoples R China
关键词
D O I
10.1246/cl.2005.1220
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
Three representative spirostanol saponins that have typical structure of the sugar moiety, diosgenyl 2,3-di-O-alpha-(L)-rhamnopyranosyl-beta-(D)-glucopyranoside, diosgenyl 2,4-di-O-alpha-(L)-rhamnopyranosyl- beta-(D)-glucopyranoside (dioscin), and diosgenyl 2,6di-O-alpha-(L)-rhamnopyranosyl- beta-(D)-glucopyranoside, were synthesized in a facile way. An approach to selectively mask the C-3-hydroxyl of diosgenyl 4,6-O-benzylidene beta-(D)-glucopyranoside was described. A procedure using cerium(IV) ammonium nitrate for selective removal of tert-butyldimethylsilyl group while retaining levulinyl group is afforded.
引用
收藏
页码:1220 / 1221
页数:2
相关论文
共 16 条
[1]
Selective deprotection of either alkyl or aryl silyl ethers from aryl, alkyl bis-silyl ethers [J].
Ankala, SV ;
Fenteany, G .
TETRAHEDRON LETTERS, 2002, 43 (27) :4729-4732
[2]
Deprotection of t-butyldimethylsilyl ethers promoted by cerium(IV) triflate [J].
Bartoli, G ;
Cupone, G ;
Dalpozzo, R ;
De Nino, A ;
Maiuolo, L ;
Procopio, A ;
Sambri, L ;
Tagarelli, A .
TETRAHEDRON LETTERS, 2002, 43 (34) :5945-5947
[3]
SPIROSTANIC DIOSGENIN PRECURSORS FROM DIOSCOREA-COMPOSITA TUBERS [J].
ESPEJO, O ;
LLAVOT, JC ;
JUNG, H ;
GIRAL, F .
PHYTOCHEMISTRY, 1982, 21 (02) :413-416
[4]
SIMPLE METHOD FOR THE SYNTHESIS OF ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-RHAMNOPYRANOSIDE [J].
FUJIWARA, T ;
ARAI, K .
CARBOHYDRATE RESEARCH, 1979, 69 (MAR) :305-307
[5]
Greene T. W., 1999, PROTECTIVE GROUPS OR
[6]
Hostettmann K., 1995, SAPONINS
[7]
Hou SR, 2005, CHINESE CHEM LETT, V16, P593
[8]
KHANNA I, 1975, INDIAN J CHEM, V13, P781
[9]
KITAGAWA I, 1989, CHEM PHARM BULL, V37, P1131, DOI 10.1248/cpb.37.1131
[10]
Synthesis of diosgenyl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (gracillin) and related saponins [J].
Li, C ;
Yu, B ;
Liu, MZ ;
Hui, YZ .
CARBOHYDRATE RESEARCH, 1998, 306 (1-2) :189-195