methyl (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16S,20R,21S,22S,23Z)-7,9,13-tris[[tert-butyl(dimethyl)silyl]oxy]-21-hydroxy-6,12,14,16,20,22-hexamethyl-19-oxohexacosa-2,4,10,23,25-pentaenoate | 1075200-53-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16S,20R,21S,22S,23Z)-7,9,13-tris[[tert-butyl(dimethyl)silyl]oxy]-21-hydroxy-6,12,14,16,20,22-hexamethyl-19-oxohexacosa-2,4,10,23,25-pentaenoate
• CAS: 1075200-53-1
• 化学式: C₅₁H₉₆O₇Si₃
• 分子量: 905.576
• InChiKey: LHOMYIKSTAXLIX-POSJNCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.05
• 重原子数：
  61
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16S,20R,21S,22S,23Z)-7,9,13-tris[[tert-butyl(dimethyl)silyl]oxy]-21-hydroxy-6,12,14,16,20,22-hexamethyl-19-oxohexacosa-2,4,10,23,25-pentaenoate 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 以0.2 g的产率得到(2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16S,19R,20S,21S,22S,23Z)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-19,21-dihydroxy-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate
  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,16S,20R,21S,22S,23Z)-methyl 7,9,13-tris(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethyl-19-oxohexacosa-2,4,10,23,25-pentaenoate 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， 生成 methyl (2Z,4E,6S,7S,9S,10Z,12S,13R,14S,16S,20R,21S,22S,23Z)-7,9,13-tris[[tert-butyl(dimethyl)silyl]oxy]-21-hydroxy-6,12,14,16,20,22-hexamethyl-19-oxohexacosa-2,4,10,23,25-pentaenoate
  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

文献信息

• Improved Synthesis of 6-<i>epi</i>-Dictyostatin and Antitumor Efficacy in Mice Bearing MDA-MB231 Human Breast Cancer Xenografts
  作者：Julie L. Eiseman、Lihua Bai、Won-Hyuk Jung、Gustavo Moura-Letts、Billy W. Day、Dennis P. Curran

  DOI：10.1021/jm800979v

  日期：2008.11.13

  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.