2,2-Dimethyl-propionic acid (2S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester | 205372-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-Dimethyl-propionic acid (2S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester
• 英文别名: [(2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxyhept-6-enyl] 2,2-dimethylpropanoate
• CAS: 205372-02-7
• 化学式: C₂₅H₄₂O₄Si
• 分子量: 434.692
• InChiKey: XDEMCYKECUVARC-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙二醇 、 2,2-Dimethyl-propionic acid (2S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester 在 mercury(II) diacetate 、 lithium carbonate 、 对甲苯磺酸 、 copper(l) chloride 、 lithium chloride 、 palladium dichloride 作用下， 生成 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-(2-methyl-[1,3]dioxolan-2-yl)-pentyl ester
  参考文献：
  名称：

  A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal

  摘要：

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.

  DOI：

  10.3987/com-97-s(n)7
• 作为产物：
  描述：

  (2S,4R)-4-Benzyloxy-hept-6-ene-1,2-diol 在 吡啶 、 2,6-二甲基吡啶 作用下， 反应 4.33h， 生成 2,2-Dimethyl-propionic acid (2S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester
  参考文献：
  名称：

  A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal

  摘要：

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.

  DOI：

  10.3987/com-97-s(n)7

文献信息

• A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal
  作者：Takayuki Shioiri、Nigel McFarlane、Yasumasa Hamada

  DOI：10.3987/com-97-s(n)7

  日期：——

  AC(1)-C-7 building block (4) for the enantiomer of hennoxazole A (1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.