ethyl (S)-6-methyl-2E-octenoate | 170156-93-1

• 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: ethyl (S)-6-methyl-2E-octenoate
• 英文别名: ethyl (E,6S)-6-methyloct-2-enoate
• CAS: 170156-93-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: QZCXQIZSDXGRKO-PCYYEKQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (S)-6-methyl-2E-octenoate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 以95%的产率得到(S)-6-methyl-2E-octen-1-ol
  参考文献：
  名称：

  Approaches towards the synthesis of papulacandin D: preparation and structural elucidation of the acyl side chain

  摘要：

  通过L-(+)-异亮氨酸的降解和全合成来确定papulacandin D的O-3′-酰基侧链的绝对立体化学。

  DOI：

  10.1039/c39950001145
• 作为产物：
  描述：

  (S)-3-methylpentyl p-toluenesulfonate 在 magnesium 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 ethyl (S)-6-methyl-2E-octenoate
  参考文献：
  名称：

  Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D

  摘要：

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).

  DOI：

  10.1021/jo951895e

文献信息

• Approaches towards the synthesis of papulacandin D: preparation and structural elucidation of the acyl side chain
  作者：Anthony G. M. Barrett、Michael Peña、J. Adam Willardsen

  DOI：10.1039/c39950001145

  日期：——

  Both degradation and total synthesis from L-(+)-isoleucine are used to establish the absolute stereochemistry of the O-3′-acyl side chain of papulacandin D.

  通过L-(+)-异亮氨酸的降解和全合成来确定papulacandin D的O-3′-酰基侧链的绝对立体化学。
• Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D
  作者：Anthony G. M. Barrett、Michael Peña、J. Adam Willardsen

  DOI：10.1021/jo951895e

  日期：1996.1.1

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).