(2Z,4E,6S,7S,9S)-methyl 7-(tert-butyldimethylsilyloxy)-9-hydroxy-6-methylundeca-2,4,10-trienoate | 1075200-46-2

• 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: (2Z,4E,6S,7S,9S)-methyl 7-(tert-butyldimethylsilyloxy)-9-hydroxy-6-methylundeca-2,4,10-trienoate
• 英文别名: methyl (2Z,4E,6S,7S,9S)-7-[tert-butyl(dimethyl)silyl]oxy-9-hydroxy-6-methylundeca-2,4,10-trienoate
• CAS: 1075200-46-2
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: BICZJFMCCKGRAE-OOIPICRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 (2Z,4E,6S,7S,9S)-methyl 7-(tert-butyldimethylsilyloxy)-9-hydroxy-6-methylundeca-2,4,10-trienoate 、 (2Z,4E,6S,7S,9R)-methyl 7-(tert-butyldimethylsilyloxy)-9-hydroxy-6-methylundeca-2,4,10-trienoate
  参考文献：
  名称：

  Improved Synthesis of 6-epi-Dictyostatin and Antitumor Efficacy in Mice Bearing MDA-MB231 Human Breast Cancer Xenografts

  摘要：

  Structure-activity Studies centered oil the naturally occurring antitumor agent dictyostatin have recently identified several highly active epimers and analogues. From these compounds, 6-epi-dictyostatin was selected for scaleup preparation and evaluation in animals. Here we describe a new total synthesis that produced more than 30 mg of 6-epi-diclyostatin. The compound was found to have potent antitumor activity in SCID mice bearing MDA-MB231 human breast cancer xenografts.

  DOI：

  10.1021/jm800979v