ethyl (E,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-hex-2-enoate | 871110-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (E,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-hex-2-enoate
• 英文别名: ethyl (E,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-(4-methoxyphenoxy)hex-2-enoate
• CAS: 871110-56-4
• 化学式: C₂₁H₃₄O₅Si
• 分子量: 394.583
• InChiKey: ZSCUXCSWOLPIGZ-OPUXSOHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-hex-2-enoate 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以85%的产率得到ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p
• 作为产物：
  描述：

  ethyl (E)-3-[(4S,5S)-5-methyl-2-oxo-1,3-dioxolan-4-yl]prop-2-enoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl (E,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-hex-2-enoate
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p

文献信息

• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.