diosgenyl 2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside | 335591-64-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: diosgenyl 2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)-5-hydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-2-methyloxan-3-yl] benzoate
• CAS: 335591-64-5
• 化学式: C₇₀H₉₀O₁₇
• 分子量: 1203.47
• InChiKey: JPXCVXQOHLIKLK-YAPFKCEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  87
• 可旋转键数：
  20
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  207
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  diosgenyl 2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到重楼皂苷E
  参考文献：
  名称：

  在Ga（OTf）3，In（OTf）3或HOTf存在下通过金（I）催化的糖基化合成螺旋甾烷醇皂苷

  摘要：

  An effective approach relying on a Lewis acid‐ or Brønsted 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

  DOI：

  10.1002/cjoc.201900126
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate 、 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 0.83h， 以60%的产率得到diosgenyl 2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  在Ga（OTf）3，In（OTf）3或HOTf存在下通过金（I）催化的糖基化合成螺旋甾烷醇皂苷

  摘要：

  An effective approach relying on a Lewis acid‐ or Brønsted 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

  DOI：

  10.1002/cjoc.201900126

文献信息

• Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
  作者：Xin Meng、Yiwu Pan、Tao Liu、Chen Luo、Shuli Man、Yongmin Zhang、Yan Zhang

  DOI：10.1016/j.carres.2021.108359

  日期：2021.8

  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

  薯蓣皂苷是一类从植物中提取的天然产物，是中药的主要活性成分。令人鼓舞的是，大量天然薯蓣皂苷已被证明对肝细胞癌细胞（HCC）具有极好的毒性。为了更好地理解其结构与其生物效应之间的关系，高效合成了一组薯蓣皂苷（ 1-4为天然产物， 5和6为其类似物）。在人肝细胞癌 (HepG2) 细胞上评估了这些化合物的细胞毒活性。构效关系研究表明，五糖或六糖皂苷类似物的活性比相应的二糖类似物或薯蓣皂苷的活性相对较低。这些皂苷上4支链鼠李糖部分的延伸对其细胞毒活性没有表现出明显的影响，这表明一定数量的鼠李糖部分和连接方式可以影响类固醇皂苷对HepG2细胞的细胞毒性。
• Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives
  作者：Zhiqi Yang、Ella Lai-Ming Wong、Tina Yuen-Ting Shum、Chi-Ming Che、Yongzheng Hui

  DOI：10.1021/ol0475616

  日期：2005.2.1

  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 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.
• An improved synthesis of the saponin, polyphyllin D
  作者：Bing Li、Biao Yu*、Yongzheng Hui*、Ming Li、Xiuwen Han、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(01)00014-3

  日期：2001.3

  Polyphyllin D, namely diosgenyl alpha -L-rhamnopyranosyl-(1->2)-[(alpha -L-arabinofuranosyl)-(1->4)]-beta -D-glucopyranoside, was synthesized from diosgenyl-beta -D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha -L-rhamnopyranosylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.