[(2S,3S)-3-[dimethyl(phenyl)silyl]-1-methoxypent-4-en-2-yl]oxy-trimethylsilane | 674335-96-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(2S,3S)-3-[dimethyl(phenyl)silyl]-1-methoxypent-4-en-2-yl]oxy-trimethylsilane
• CAS: 674335-96-7
• 化学式: C₁₇H₃₀O₂Si₂
• 分子量: 322.595
• InChiKey: LJDXXBXMIFHYIS-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-[dimethyl(phenyl)silyl]-1-methoxypent-4-en-2-yl]oxy-trimethylsilane 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 51.17h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,4S,6R)-2-benzyl-6-methoxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Total Synthesis of (−)-Apicularen A

  摘要：

  Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.

  DOI：

  10.1021/ja037957x
• 作为产物：
  描述：

  [(2S,3S)-3-(dimethyl-phenyl-silanyl)-oxiran-2-yl]methanol 在 吡啶 、 sodium hydroxide 、 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.92h， 生成 [(2S,3S)-3-[dimethyl(phenyl)silyl]-1-methoxypent-4-en-2-yl]oxy-trimethylsilane
  参考文献：
  名称：

  Total Synthesis of (−)-Apicularen A

  摘要：

  Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.

  DOI：

  10.1021/ja037957x

文献信息

• Total Synthesis of (−)-Apicularen A
  作者：Qibin Su、James S. Panek

  DOI：10.1021/ja037957x

  日期：2004.3.3

  Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.