Methyl 17-(2-tetrahydro-2H-pyran-2-yloxy)-5(Z),8(Z)-heptadecadienoate | 162008-62-0

• 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: Methyl 17-(2-tetrahydro-2H-pyran-2-yloxy)-5(Z),8(Z)-heptadecadienoate
• 英文别名: methyl (5Z,8Z)-17-(oxan-2-yloxy)heptadeca-5,8-dienoate
• CAS: 162008-62-0
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: UCNYYIMPKHEGII-VBFFHFTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 17-(2-tetrahydro-2H-pyran-2-yloxy)-5(Z),8(Z)-heptadecadienoate 在 jones reagent 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 9(Z),12(Z)-Heptadecadiendioic acid 17-methyl ester
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037
• 作为产物：
  描述：

  12-(四氢-2H-吡喃-2-基氧基)-3-十二碳炔-1-醇 在 咪唑 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 氢气 、 碘 、 nickel diacetate 、 乙二胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 乙醚 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 54.5h， 生成 Methyl 17-(2-tetrahydro-2H-pyran-2-yloxy)-5(Z),8(Z)-heptadecadienoate
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037

文献信息

• A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE
  作者：Patrick Dussault、In Quen Lee

  DOI：10.1021/jo00106a037

  日期：1995.1

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.