(2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-17-(4-methoxybenzyloxy)-6,12,14,16-tetramethylheptadeca-2,4,10-trienoate | 1075200-57-5

• 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: (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-17-(4-methoxybenzyloxy)-6,12,14,16-tetramethylheptadeca-2,4,10-trienoate
• CAS: 1075200-57-5
• 化学式: C₄₈H₈₈O₇Si₃
• 分子量: 861.479
• InChiKey: JGZASUGINVIQCQ-XYULNYROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.55
• 重原子数：
  58.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-17-(4-methoxybenzyloxy)-6,12,14,16-tetramethylheptadeca-2,4,10-trienoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以73%的产率得到(2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-17-hydroxy-6,12,14,16-tetramethylheptadeca-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
• 作为产物：
  描述：

  (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7-(tert-butyldimethylsilyloxy)-9,13-dihydroxy-17-(4-methoxybenzyloxy)-6,12,14,16-tetramethylheptadeca-2,4,10-trienoate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16R)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-17-(4-methoxybenzyloxy)-6,12,14,16-tetramethylheptadeca-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