(SS,S)-2-allyl-6-(tert-butyldimethylsilyloxy)-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman | 1206474-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (SS,S)-2-allyl-6-(tert-butyldimethylsilyloxy)-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman
• 英文别名: tert-butyl-[[(2S)-7,8-dimethyl-2-[[(S)-(4-methylphenyl)sulfinyl]methyl]-2-prop-2-enyl-3,4-dihydrochromen-6-yl]oxy]-dimethylsilane
• CAS: 1206474-44-3
• 化学式: C₂₈H₄₀O₃SSi
• 分子量: 484.775
• InChiKey: KGVVVUQWHIEQMZ-NSJVFKKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (SS,S)-2-allyl-6-(tert-butyldimethylsilyloxy)-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (S)-γ-CEHC [(S)-LLU-α]

  摘要：

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.

  DOI：

  10.1021/ol9027804
• 作为产物：
  描述：

  二甲基烯丙基硅烷 、 (SS)-6-(tert-butyldimethylsilyloxy)-2-methoxy-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以67%的产率得到(SS,S)-2-allyl-6-(tert-butyldimethylsilyloxy)-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (S)-γ-CEHC [(S)-LLU-α]

  摘要：

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.

  DOI：

  10.1021/ol9027804

文献信息

• Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (<i>S</i>)-γ-CEHC [(<i>S</i>)-LLU-α]
  作者：Mercedes Lecea、Gloria Hernández-Torres、Antonio Urbano、M. Carmen Carreño、Françoise Colobert

  DOI：10.1021/ol9027804

  日期：2010.2.5

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.