503314-24-7Relevant academic research and scientific papers
A facile approach to diosgenin and furostan type saponins bearing a 3β-chacotriose moiety
Lahmann, Martina,Gybaeck, Helena,Garegg, Per J.,Oscarson, Stefan,Suhr, Rene,Thiem, Joachim
, p. 2153 - 2159 (2002)
Combination of a one-pot coupling technique and the use of benzyl ethers as permanent protecting groups offered a short and simple route to dioscin-type saponins. This strategy in combination with a mild reductive opening procedure of the spiroketal function in diosgenin also offered a convenient approach to bidesmosidic furostan type saponins. Me3N·BH3/AlCl3 promoted acetal opening of 3-O-TBDMS-protected diosgenin gave the 26-OH acceptor 9 into which a benzylated β-glucose moiety was introduced by a SN2-type imidate coupling. After cleavage of the silyl ether, the 3β-O-glucose and the 4-O-linked rhamnose of the chacotriose unit were introduced by a NIS/AgOTf-promoted one-pot coupling sequence utilising thioglycoside donors and their different reactivity in different solvents. After removal of a benzoyl group, the same coupling conditions were also used for the coupling of the second 2-O-linked rhamnose unit. The target substance was obtained after cleavage of the protecting benzyl ethers under Birch-type conditions, which did not affect the double bond in the steroid skeleton.
Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives
Yang, Zhiqi,Wong, Ella Lai-Ming,Shum, Tina Yuen-Ting,Che, Chi-Ming,Hui, Yongzheng
, p. 669 - 672 (2007/10/03)
(Chemical Equation Presented) The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 μM) against the HeLa carcinoma cell line evaluated by standard MTT assay.
