(2S,2'S,5'S)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one | 862557-19-5

• 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: (2S,2'S,5'S)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one
• 英文别名: (5S)-5-[(2S,5S)-5-[(E,1S)-1-hydroxy-8-phenylmethoxyoct-4-enyl]oxolan-2-yl]oxolan-2-one
• CAS: 862557-19-5
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: BDIOUTVMNFEQJR-DXVOJMDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,2'S,5'S)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one 在 L-fructose-based (+)-Shi catalyst 、 四丁基硫酸氢铵 Sodium tetraborate decahydrate 、 Oxone 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 生成 (2S,2'S,5'S)-5'-{(S)-3-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-1-hydroxy-propyl}-tetrahydro-[2,2']bifuranyl-5-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
• 作为产物：
  描述：

  (4E,8E)-(R)-12-Benzyloxy-1-(S)-oxiranyl-dodeca-4,8-dien-1-ol 在 2,6-二甲基吡啶 、 sodium hydroxide 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 对甲苯磺酸 、 rhenium(VII) oxide 、 二异丙胺 、 三苯基膦 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.42h， 生成 (2S,2'S,5'S)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-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.