(1S,2S,Z)-2-(4-(tert-butylmethoxysilyloxy)but-2-enyloxy)-1,2-diphenylethanol | 1233481-72-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S,Z)-2-(4-(tert-butylmethoxysilyloxy)but-2-enyloxy)-1,2-diphenylethanol
• 英文别名: (1S,2S)-2-[(Z)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enoxy]-1,2-diphenylethanol
• CAS: 1233481-72-5
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: BIFJGSVIMFLYAP-HJCBPWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (1S,2S,Z)-2-(4-(tert-butylmethoxysilyloxy)but-2-enyloxy)-1,2-diphenylethanol 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 tert-butyl((S)-2-((2R,5S,6S)-5,6-diphenyl-1,4-dioxan-2-yl)-2-iodoethoxy)dimethylsilane 、 tert-butyl((S)-2-((2S,5S,6S)-5,6-diphenyl-1,4-dioxan-2-yl)-2-iodoethoxy)dimethylsilane
  参考文献：
  名称：

  A concise enantioselective total synthesis of (+)-epi-muricatacin, using asymmetric hydrogenation/intramolecular iodoetherification as key steps

  摘要：

  A concise enantioselective total synthesis of (+)-epi-muricatacin, a potent cytotoxic agent, is described. A key feature of this protocol is a catalytic asymmetric hydrogenation and a chiral auxiliary mediated intramolecular iodoetherification to ensure a high degree of distereo- and enantiocontrol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.024
• 作为产物：
  描述：

  联苯甲酰 、 (2Z)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl methane-sulfonate 在 Noyori's catalyst 、 甲酸 、 三乙胺 、 sodium hydride 作用下， 以 四氢呋喃 、 oil 为溶剂， 反应 24.5h， 以70%的产率得到(1S,2S,Z)-2-(4-(tert-butylmethoxysilyloxy)but-2-enyloxy)-1,2-diphenylethanol
  参考文献：
  名称：

  A concise enantioselective total synthesis of (+)-epi-muricatacin, using asymmetric hydrogenation/intramolecular iodoetherification as key steps

  摘要：

  A concise enantioselective total synthesis of (+)-epi-muricatacin, a potent cytotoxic agent, is described. A key feature of this protocol is a catalytic asymmetric hydrogenation and a chiral auxiliary mediated intramolecular iodoetherification to ensure a high degree of distereo- and enantiocontrol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.024

文献信息

• A concise enantioselective total synthesis of (+)-epi-muricatacin, using asymmetric hydrogenation/intramolecular iodoetherification as key steps
  作者：Gullapalli Kumaraswamy、Duggirala Ramakrishna、Kondapalli Santhakumar

  DOI：10.1016/j.tetasy.2010.02.024

  日期：2010.3

  A concise enantioselective total synthesis of (+)-epi-muricatacin, a potent cytotoxic agent, is described. A key feature of this protocol is a catalytic asymmetric hydrogenation and a chiral auxiliary mediated intramolecular iodoetherification to ensure a high degree of distereo- and enantiocontrol. (C) 2010 Elsevier Ltd. All rights reserved.