(4R,5S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-3,4-dimethylhepta-2,6-dienoate | 1373432-35-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,5S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-3,4-dimethylhepta-2,6-dienoate
• CAS: 1373432-35-9
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: SBJGRKHQYKIMSB-GIQRUMHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-3,4-dimethylhepta-2,6-dienoate 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以84%的产率得到(4R,5S,Z)-5-(tert-butyldimethylsilyloxy)-3,4-dimethylhepta-2,6-dienoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

  摘要：

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

  DOI：

  10.1021/ol300785c
• 作为产物：
  描述：

  (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpent-4-en-1-one 在 2,6-二甲基吡啶 、 copper(l) iodide 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 (4R,5S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-3,4-dimethylhepta-2,6-dienoate
  参考文献：
  名称：

  Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

  摘要：

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

  DOI：

  10.1021/ol300785c