(S)-2-(trimethylsilyl)ethyl 3,4-bis(tert-butyldimethylsilyloxy)butanoate | 1217361-97-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-(trimethylsilyl)ethyl 3,4-bis(tert-butyldimethylsilyloxy)butanoate
• 英文别名: 2-trimethylsilylethyl (3S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]butanoate
• CAS: 1217361-97-1
• 化学式: C₂₁H₄₈O₄Si₃
• 分子量: 448.866
• InChiKey: FBBIDDCLIYMXHE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(trimethylsilyl)ethyl 3,4-bis(tert-butyldimethylsilyloxy)butanoate 在 camphor-10-sulfonic acid 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 2-(trimethylsilyl)ethyl (S)-3-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanoate
  参考文献：
  名称：

  Stereoselective Synthesis of (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7- (tritylthio)hept-4-enoate

  摘要：

  (S,E)-2-(三甲基硅基)乙基 3-羟基-7-(三苯甲硫基)庚-4-烯酸酯是通过商业可得的L-苹果酸，采用Julia-Kocienski 烯化偶联方法合成的。该方法为(S,E)-3-羟基-7-巯基庚-4-烯酸提供了一种简洁的合成策略。

  DOI：

  10.2174/157017811794557868
• 作为产物：
  描述：

  methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate 在 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-2-(trimethylsilyl)ethyl 3,4-bis(tert-butyldimethylsilyloxy)butanoate
  参考文献：
  名称：

  Largazole Arrests Cell Cycle at G1 Phase and Triggers Proteasomal Degradation of E2F1 in Lung Cancer Cells

  摘要：

  Aberration in cell cycle has been shown to be a common occurrence in lung cancer, and cell cycle inhibitor represents an effective therapeutic strategy. In this study, we test the effects of a natural macrocyclic depsipeptide largazole on lung cancer cells and report that this compound potently inhibits the proliferation and clonogenic activity of lung cancer cells but not normal bronchial epithelial cells. Largazole arrests cell cycle at G1 phase with up-regulation of the expression of cyclin-dependent kinase inhibitor p21. Interestingly, largazole enhances the E2F1-HDAC1 binding affinity and induces a proteasomal degradation of E2F1, leading to suppression of E2F1 function in lung cancer but not normal bronchial epithelial cells. Because E2F1 is overexpressed in lung cancer tumor samples, these data indicate that largazole is an E2F1-targeting cell cycle inhibitor, which bears therapeutic potentials for this malignant neoplasm.

  DOI：

  10.1021/ml400093y

文献信息

• 10.1021/01100308a
  作者：Zeng, Xin、Yin, Biaolin、Hu, Zheng、Liao, Chenzhong、Liu, Jinglei、Li, Shang、Li, Zheng、Nicklaus, Marc C.、Zhou, Guangbiao、Jiang, Sheng

  DOI：10.1021/01100308a

  日期：——
• Largazole Arrests Cell Cycle at G1 Phase and Triggers Proteasomal Degradation of E2F1 in Lung Cancer Cells
  作者：Li-Chuan Wu、Zhe-Sheng Wen、Ya-Tao Qiu、Xiao-Qin Chen、Hao-Bin Chen、Ming-Ming Wei、Zi Liu、Sheng Jiang、Guang-Biao Zhou

  DOI：10.1021/ml400093y

  日期：2013.10.10

  Aberration in cell cycle has been shown to be a common occurrence in lung cancer, and cell cycle inhibitor represents an effective therapeutic strategy. In this study, we test the effects of a natural macrocyclic depsipeptide largazole on lung cancer cells and report that this compound potently inhibits the proliferation and clonogenic activity of lung cancer cells but not normal bronchial epithelial cells. Largazole arrests cell cycle at G1 phase with up-regulation of the expression of cyclin-dependent kinase inhibitor p21. Interestingly, largazole enhances the E2F1-HDAC1 binding affinity and induces a proteasomal degradation of E2F1, leading to suppression of E2F1 function in lung cancer but not normal bronchial epithelial cells. Because E2F1 is overexpressed in lung cancer tumor samples, these data indicate that largazole is an E2F1-targeting cell cycle inhibitor, which bears therapeutic potentials for this malignant neoplasm.
• Stereoselective Synthesis of (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7- (tritylthio)hept-4-enoate
  作者：Zhiyi Yao、Xin Zeng、Wei Yi、Sheng Jiang

  DOI：10.2174/157017811794557868

  日期：2011.1.1

  (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7-(tritylthio)hept-4-enoate was synthesized from commercially available L-malic acid by the Julia-Kocienski olefination coupling method. This method provides a concise synthetic strategy for (S,E) -3-hydroxy-7-mercaptohept-4-enoic acid.

  (S,E)-2-(三甲基硅基)乙基 3-羟基-7-(三苯甲硫基)庚-4-烯酸酯是通过商业可得的L-苹果酸，采用Julia-Kocienski 烯化偶联方法合成的。该方法为(S,E)-3-羟基-7-巯基庚-4-烯酸提供了一种简洁的合成策略。