335591-64-5

Upstream product

• 14218-08-7 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 335591-63-4 diosgen-3-yl 3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 1391992-92-9 2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate 

Downstream Products

• 19057-67-1 ophiopogonin C 

Relevant academic research and scientific papers

Synthesis of spirostanol saponins via gold(I)-catalyzed glycosylation in the presence of Ga(OTf)3, In(OTf)3, or HOTf

An effective approach relying on a Lewis acid- or Br?nsted acid-assisted gold(I)-catalyzed glycosylation has been reported in the synthesis of a panel of the representative natural spirostanol saponins, namely polyphyllin D (1), polyphyllin V (2), dioscin (3), formosanin C (4), and a derivative of polyphyllin D bearing a terminal azide group (5). This approach highlights the engagement of low loadings of Ph3AuPOTf (≤ 0.5 mol%) in the presence of Ga(OTf)3, In(OTf)3, or HOTf (~10mol%) as a co-catalyst, at practical reaction rates as an alternative to the conventional ~10 mol% loadings of the gold(I) catalyst in the glycosylation. Polyphyllin D (1) was obtained in 41% overall yield over six steps compared to the maximum 30% yield in previous syntheses where conventional donors and promoters were used. By exploiting a regioselective rhamnosylation, a “one-pot” approach was adopted to assemble 1 and 5, thus further strengthening the efficiency of the gold(I)-catalyzed glycosylation.

An improved synthesis of the saponin, polyphyllin D

Polyphyllin D, namely diosgenyl α-L-rhamnopyranosyl-(1→2)-[(α-L-arabinofuranosyl)- (1→4)]-β-D-glucopyranoside, was synthesized from diosgenyl-β-D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and

Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity

Diosgenyl saponins, as a type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products and 5 and 6 as their analogs) were efficiently synthesized. The cytotoxic activity of these compounds was evaluated on human hepatocellular carcinoma (HepG2) cells. Structure–activity relationship studies showed that the pentasaccharide or hexasaccharide saponin analogs were relatively less active than their corresponding disaccharide analogue or dioscin. The extension of 4-branched rhamnose moiety on these saponin does not exhibit significant effect on their cytotoxic activity, which disclosed that a certain number and the linkage mode of rhamnose moieties could influence the cytotoxicity of steroid saponins on HepG2 cells.

Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives

(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.