(2E,4E)-5-((4R,5R)-5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-penta-2,4-dienoic acid methyl ester | 485323-90-8

• 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: (2E,4E)-5-((4R,5R)-5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-penta-2,4-dienoic acid methyl ester
• 英文别名: methyl (2E,4E)-5-[(4R,5R)-5-methyl-2-oxo-1,3-dioxolan-4-yl]penta-2,4-dienoate
• CAS: 485323-90-8
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: YVOKHXZVDKXPKW-OPFKOPFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-((4R,5R)-5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-penta-2,4-dienoic acid methyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 甲酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (7R)-7-hydroxy-octa-2,4-dienoic acid methyl ester 、 (7R)-7-hydroxy-octa-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502
• 作为产物：
  描述：

  6,7-dihydroxy-octa-2,4-dienoic acid methyl ester 、 三光气 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以88%的产率得到(2E,4E)-5-((4R,5R)-5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-penta-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502

文献信息

• Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A
  作者：Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/ol0269502

  日期：2002.12.1

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.