Acetic acid (2S,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester | 909130-18-3

• 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: Acetic acid (2S,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester
• CAS: 909130-18-3
• 化学式: C₃₅H₅₈O₅Si
• 分子量: 586.928
• InChiKey: BEXKZISSWYTLIJ-SVGWWTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Synthesis and antitumor activity of icogenin and its analogue

  摘要：

  Natural saponin icogenin, namely 25(S)-22-O-methyl-furost-5-en-3 beta,26-dio-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside, and one of its analogues, 25(S)-22-O-methyl-furost-5-en-3 beta,26-dio-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-alpha-D-glucopyranoside, were first synthesized via line strategy and convergent approach, respectively. It was observed that icogenin and its analogue show potent antitumor activity in vitro. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.074
• 作为产物：
  描述：

  薯蓣皂素 在 咪唑 、 4-二甲氨基吡啶 、 Oxone 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.25h， 生成 Acetic acid (2S,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of icogenin and its analogue

  摘要：

  Natural saponin icogenin, namely 25(S)-22-O-methyl-furost-5-en-3 beta,26-dio-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside, and one of its analogues, 25(S)-22-O-methyl-furost-5-en-3 beta,26-dio-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-alpha-D-glucopyranoside, were first synthesized via line strategy and convergent approach, respectively. It was observed that icogenin and its analogue show potent antitumor activity in vitro. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.074