(S)-2-Benzyloxy-4-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester | 910484-37-6

• 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-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester
• 英文别名: methyl (2S,4E)-4-[(5R,6R)-6-(hydroxymethyl)-2-methyl-5-propan-2-ylcyclohex-2-en-1-ylidene]-2-methyl-2-phenylmethoxybutanoate
• CAS: 910484-37-6
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: BPDZIWDONRIUHL-LCWLIJILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxy-4-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester 在 甲基磺酰胺 、 potassium carbonate 四氧化锇 、 草酰氯 、 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 62.0h， 生成 (S)-4-[(2R,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2-hydroxy-5-isopropyl-2-methyl-3-oxo-cyclohex-(E)-ylidene]-2-benzyloxy-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：

  (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester 在 RhCl(PPh₃)3 盐酸 、 氢气 作用下， 以 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

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.