methyl (Z)-3-[(1S,2S,4aS,5S,8S,8aS)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,8-dimethyl-5-tri(propan-2-yl)silyloxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-2-enoate | 1110702-86-7

• 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: methyl (Z)-3-[(1S,2S,4aS,5S,8S,8aS)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,8-dimethyl-5-tri(propan-2-yl)silyloxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-2-enoate
• CAS: 1110702-86-7
• 化学式: C₄₃H₆₆O₄Si₂
• 分子量: 703.166
• InChiKey: UBAUQKVKXIVBHW-XDKQGDSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-[(1S,2S,4aS,5S,8S,8aS)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,8-dimethyl-5-tri(propan-2-yl)silyloxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到
  参考文献：
  名称：

  Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

  摘要：

  The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. in this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted sidechain alkene. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.138
• 作为产物：
  描述：

  methyl (E)-3-[(1S,2S,4aS,5S,8S,8aS)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,8-dimethyl-5-tri(propan-2-yl)silyloxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]-3-diphenoxyphosphoryloxyprop-2-enoate 、 methylzinc chloride 在 (1,2-bis(diphenylphosphino)ethane)nickel(II) chloride 作用下， 以 苯 为溶剂， 反应 1.0h， 以19%的产率得到methyl (Z)-3-[(1S,2S,4aS,5S,8S,8aS)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,8-dimethyl-5-tri(propan-2-yl)silyloxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-2-enoate
  参考文献：
  名称：

  Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

  摘要：

  The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. in this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted sidechain alkene. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.138

文献信息

• Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene
  作者：Nobuyuki Hayashi、Masahisa Nakada

  DOI：10.1016/j.tetlet.2008.10.138

  日期：2009.1

  The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. in this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted sidechain alkene. (c) 2008 Elsevier Ltd. All rights reserved.