methyl (S)-3-((1S,2S,4aS,5S,8S,8aS)-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,8-dimethyl-5-((triisopropylsilyl)oxy)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-3-hydroxypropanoate | 1110703-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (S)-3-((1S,2S,4aS,5S,8S,8aS)-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,8-dimethyl-5-((triisopropylsilyl)oxy)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-3-hydroxypropanoate
• CAS: 1110703-10-0
• 化学式: C₄₂H₆₆O₅Si₂
• 分子量: 707.154
• InChiKey: OWBFXNSIJLUNOF-CPHMGSLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-((1S,2S,4aS,5S,8S,8aS)-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,8-dimethyl-5-((triisopropylsilyl)oxy)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-3-hydroxypropanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以80%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
• 作为产物：
  描述：

  乙酸甲酯 、 (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-octahydronaphthalene-2-carbaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到methyl (S)-3-((1S,2S,4aS,5S,8S,8aS)-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,8-dimethyl-5-((triisopropylsilyl)oxy)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-3-hydroxypropanoate
  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