8-(4-methoxy-benzyloxy)-3,5,7-trimethyl-oct-1-en-4-ol | 887602-17-7

• 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: 8-(4-methoxy-benzyloxy)-3,5,7-trimethyl-oct-1-en-4-ol
• 英文别名: (3S,4R,5S,7R)-8-[(4-methoxyphenyl)methoxy]-3,5,7-trimethyloct-1-en-4-ol
• CAS: 887602-17-7
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: KVTUVUXAWQBINK-DRMAHVMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(4-methoxy-benzyloxy)-3,5,7-trimethyl-oct-1-en-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 4,6-bis-(tert-butyl-dimethyl-silanyloxy)-10-[4-(4-methoxy-benzyloxy)-1,3-dimethyl-butyl]-3,9-dimethyl-3,4,5,6,9,10-hexahydro-oxecin-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Dictyostatin

  摘要：

  A convergent total synthesis of dictyostatin is described. Key features of the synthesis include the use of titanium-mediated cyclizations of (silyloxy)enynes for the synthesis of stereotriads, a subunit coupling by metathesis, and macrocyclization by intramolecular Horner-Wadsworth-Emmons olefination.

  DOI：

  10.1021/ja0609708
• 作为产物：
  描述：

  (3S,4S,6R)-7-(4-Methoxy-benzyloxy)-4,6-dimethyl-hept-1-en-3-ol 在 咪唑 、 三异丙氧基氯化钛 、 四丁基氟化铵 、 异丙基氯化镁 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 8-(4-methoxy-benzyloxy)-3,5,7-trimethyl-oct-1-en-4-ol
  参考文献：
  名称：

  Total Synthesis of (−)-Dictyostatin

  摘要：

  A convergent total synthesis of dictyostatin is described. Key features of the synthesis include the use of titanium-mediated cyclizations of (silyloxy)enynes for the synthesis of stereotriads, a subunit coupling by metathesis, and macrocyclization by intramolecular Horner-Wadsworth-Emmons olefination.

  DOI：

  10.1021/ja0609708

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.
• Total Synthesis of (−)-Dictyostatin
  作者：Gregory W. O'Nei、Andrew J. Phillips

  DOI：10.1021/ja0609708

  日期：2006.4.1

  A convergent total synthesis of dictyostatin is described. Key features of the synthesis include the use of titanium-mediated cyclizations of (silyloxy)enynes for the synthesis of stereotriads, a subunit coupling by metathesis, and macrocyclization by intramolecular Horner-Wadsworth-Emmons olefination.