(5S)-6(E),8(Z)-Heptadecadien-1,5,17-triol

• 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: (5S)-6(E),8(Z)-Heptadecadien-1,5,17-triol
• 英文别名: (5S,6E,8Z)-heptadeca-6,8-diene-1,5,17-triol
• 化学式: C₁₇H₃₂O₃
• 分子量: 284.439
• InChiKey: BEZDXOFWXYMQAZ-BEICQIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 在 咪唑 、 sodium tetrahydroborate 、 copper(I) bromide dimethylsulfide complex 、 乙基溴化镁 、 氢气 、 碘 、 氧气 、 nickel diacetate 、 对甲苯磺酸 、 乙二胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.5h， 生成 (5S)-6(E),8(Z)-Heptadecadien-1,5,17-triol
  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.