(S)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one | 862557-01-5

• 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: (S)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one
• 英文别名: (5S)-5-[(1R,4Z,8E)-1-hydroxy-12-phenylmethoxydodeca-4,8-dienyl]oxolan-2-one
• CAS: 862557-01-5
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: ABJPJQDYNQRJGD-HCDPPNFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 rhenium(VII) oxide 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid (S)-4-acetoxy-1-[(2S,5S,2'R,5'R)-5'-((S)-1,4-diacetoxy-butyl)-octahydro-[2,2']bifuranyl-5-yl]-butyl ester
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c
• 作为产物：
  描述：

  ethyl (4E)-8-benzyloxy-4-enoctanoate 在 咪唑 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 碘 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 (S)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c

文献信息

• A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins
  作者：Sanjib Das、Lian-Sheng Li、Sunny Abraham、Zhiyong Chen、Subhash C. Sinha

  DOI：10.1021/jo050697c

  日期：2005.7.1

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.