methyl 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-oxopropanoate | 1110702-82-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 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-oxopropanoate
• CAS: 1110702-82-3
• 化学式: C₄₂H₆₄O₅Si₂
• 分子量: 705.138
• InChiKey: CFLJLSYUICCHJD-GGPVZVPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.11
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 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-oxopropanoate 、 氯磷酸二苯酯 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以99%的产率得到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
  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 在 Me₂Cu(CN)Li₂ 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以55%的产率得到methyl 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-oxopropanoate
  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.