ethyl (2E,4E,8E,10E)-7-hydroxy-8-methyl-2,4,8,10-nonadecatetraenoate | 1238375-98-8

• 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: ethyl (2E,4E,8E,10E)-7-hydroxy-8-methyl-2,4,8,10-nonadecatetraenoate
• CAS: 1238375-98-8
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: FGSXDBIOAIFGNB-GQAAKMIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 ethyl (2E,4E,8E,10E)-7-hydroxy-8-methyl-2,4,8,10-nonadecatetraenoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl (2E,4Z,8E,10E)-7-triethylsiloxy-8-methyl-2,4,8,10-nonadeca-tetraenoate 、 ethyl (2E,4E,8E,10E)-7-triethylsiloxy-8-methyl-2,4,8,10-nonadecatetraenoate
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093
• 作为产物：
  描述：

  (3E)-1-ethoxy-1-(tert-butyldimethylsiloxy)-1,3,5-hexatriene 、 (2E,4E)-2-methyl-2,4-tridecadienal 在 四氯化硅 、 N,N-二异丙基乙胺 、 1,3-dimethyl-2-piperidinyl-1,3,2-diazaphospholidine-2-oxide 、 potassium fluoride 、 potassium dihydrogenphosphate 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以44%的产率得到ethyl (2E,4E,8E,10E)-7-hydroxy-8-methyl-2,4,8,10-nonadecatetraenoate
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093