(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid | 910484-44-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid
• 英文别名: (2S,4E)-4-[(5S,6R)-6-(methoxymethoxymethyl)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ylidene]-2-methyl-2-phenylmethoxybutanoic acid
• CAS: 910484-44-5
• 化学式: C₂₅H₃₄O₅
• 分子量: 414.542
• InChiKey: PXDDSFISNKSNAQ-OBSPMFKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid 在 RhCl(PPh₃)3 盐酸 、 氢气 作用下， 以 乙醚 、 异丙醇 、 苯 为溶剂， 20.0~65.0 ℃ 、241.32 kPa 条件下， 反应 34.0h， 生成 (S)-2-Benzyloxy-4-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Approach to the Synthesis of Cladiell-11-ene-3,6,7-triol

  摘要：

  The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland - Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an S(N)2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.

  DOI：

  10.1021/ol061072j
• 作为产物：
  描述：

  (3S,5S)-3-Benzyloxy-5-((S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl)-3-methyl-dihydro-furan-2-one 、 (甲氧基甲氧基甲基)三丁基锡 在 lithium chloride 正丁基锂 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以91%的产率得到(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid
  参考文献：
  名称：

  Approach to the Synthesis of Cladiell-11-ene-3,6,7-triol

  摘要：

  The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland - Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an S(N)2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.

  DOI：

  10.1021/ol061072j

文献信息

• Approach to the Synthesis of Cladiell-11-ene-3,6,7-triol
  作者：John M. Hutchison、Harriet A. Lindsay、Silvana S. Dormi、Gavin D. Jones、David A. Vicic、Matthias C. McIntosh

  DOI：10.1021/ol061072j

  日期：2006.8.1

  The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland - Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an S(N)2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.