ethyl (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxyoct-2-enoate | 1340479-52-8

• 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: ethyl (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxyoct-2-enoate
• CAS: 1340479-52-8
• 化学式: C₁₆H₃₂O₃Si
• 分子量: 300.514
• InChiKey: LZQZMMZILIKGAP-DINCDJDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxyoct-2-enoate 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxyoct-2-enal
  参考文献：
  名称：

  First stereoselective total synthesis of pectinolide A

  摘要：

  The enantioselective synthesis of bio-active 5,6-dihydro-alpha-pyrone, pectinolide A, has been achieved in 10 steps in good overall yield. Of the three stereogenic centres, the C-5/C-6 vic-diol was obtained using dia-stereo- and enantioselective Brown hydroxyl crotylation, while the C-3' stereocentre was created by Jacobsen hydrolytic kinetic resolution method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.036
• 作为产物：
  描述：

  tert-butyl-dimethyl-[(2S)-1-phenylmethoxyhexan-2-yl]oxysilane 在 草酰氯 、 20% palladium hydroxide on charcoal 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxyoct-2-enoate
  参考文献：
  名称：

  First stereoselective total synthesis of pectinolide A

  摘要：

  The enantioselective synthesis of bio-active 5,6-dihydro-alpha-pyrone, pectinolide A, has been achieved in 10 steps in good overall yield. Of the three stereogenic centres, the C-5/C-6 vic-diol was obtained using dia-stereo- and enantioselective Brown hydroxyl crotylation, while the C-3' stereocentre was created by Jacobsen hydrolytic kinetic resolution method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.036

文献信息

• First stereoselective total synthesis of pectinolide A
  作者：J.S. Yadav、S.S. Mandal

  DOI：10.1016/j.tetlet.2011.08.036

  日期：2011.11

  The enantioselective synthesis of bio-active 5,6-dihydro-alpha-pyrone, pectinolide A, has been achieved in 10 steps in good overall yield. Of the three stereogenic centres, the C-5/C-6 vic-diol was obtained using dia-stereo- and enantioselective Brown hydroxyl crotylation, while the C-3' stereocentre was created by Jacobsen hydrolytic kinetic resolution method. (C) 2011 Elsevier Ltd. All rights reserved.