(2R,6Z,9S,10E)-2-((benzyloxy)methyl)-9-((tert-butyldimethylsilyl)oxy)-10-methyl-11-(2-methylthiazol-4-yl)undeca-6,10-dienal | 1072838-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,6Z,9S,10E)-2-((benzyloxy)methyl)-9-((tert-butyldimethylsilyl)oxy)-10-methyl-11-(2-methylthiazol-4-yl)undeca-6,10-dienal
• CAS: 1072838-34-6
• 化学式: C₃₀H₄₅NO₃SSi
• 分子量: 527.844
• InChiKey: VBQWXXIQORECMJ-CNKJGDLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.39
• 重原子数：
  36.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,6Z,9S,10E)-2-((benzyloxy)methyl)-9-((tert-butyldimethylsilyl)oxy)-10-methyl-11-(2-methylthiazol-4-yl)undeca-6,10-dienal 、 (5S)-5,7-二-{[叔-丁基二甲基硅烷基)氧基]}-4,4-二甲基庚烷-3-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到(7S,10R,11S,12R,19S,Z)-12-((benzyloxy)methyl)-7-((tert-butyldimethylsilyl)oxy)-11-hydroxy-2,2,3,3,8,8,10,21,21,22,22-undecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one
  参考文献：
  名称：

  Total synthesis and evaluation of C25-benzyloxyepothilone C for tubulin assembly and cytotoxicity against MCF-7 breast cancer cells

  摘要：

  The total synthesis of C25-benzyloxy epothilone C is described. A sequential Suzuki-Aldol-Yamaguchi macrolactonization strategy was utilized employing a novel derivatized C8-C12 fragment. The C25-benzyloxy analog exhibited significantly reduced biological activity in microtubule assembly and cytotoxicity assays. Molecular modeling simulations indicated that excessive steric bulk in the C25 position may reduce activity by disrupting key hydrogen bonds that are crucial for epothilone binding to beta-tubulin. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.07.024
• 作为产物：
  描述：

  在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 以95%的产率得到(2R,6Z,9S,10E)-2-((benzyloxy)methyl)-9-((tert-butyldimethylsilyl)oxy)-10-methyl-11-(2-methylthiazol-4-yl)undeca-6,10-dienal
  参考文献：
  名称：

  Total synthesis and evaluation of C25-benzyloxyepothilone C for tubulin assembly and cytotoxicity against MCF-7 breast cancer cells

  摘要：

  The total synthesis of C25-benzyloxy epothilone C is described. A sequential Suzuki-Aldol-Yamaguchi macrolactonization strategy was utilized employing a novel derivatized C8-C12 fragment. The C25-benzyloxy analog exhibited significantly reduced biological activity in microtubule assembly and cytotoxicity assays. Molecular modeling simulations indicated that excessive steric bulk in the C25 position may reduce activity by disrupting key hydrogen bonds that are crucial for epothilone binding to beta-tubulin. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.07.024