(S)-5-[(R)-3-((2S,3S)-3-{2-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-ethyl}-oxiranyl)-1-hydroxy-propyl]-dihydro-furan-2-one | 862558-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-[(R)-3-((2S,3S)-3-{2-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-ethyl}-oxiranyl)-1-hydroxy-propyl]-dihydro-furan-2-one
• CAS: 862558-16-5
• 化学式: C₂₃H₃₂O₆
• 分子量: 404.503
• InChiKey: AEIOZJAFLWYJET-GUCLMQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  80.82
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-5-[(R)-3-((2S,3S)-3-{2-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-ethyl}-oxiranyl)-1-hydroxy-propyl]-dihydro-furan-2-one 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 Acetic acid (S)-4-acetoxy-1-[(2S,5R,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：

  (4E,8E)-dodeca-4,8-diene-1,12-diol 在 L-fructose-based (+)-Shi catalyst 、 四丁基硫酸氢铵 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 Sodium tetraborate decahydrate 、 Oxone 、 正丁基锂 、 草酰氯 、 L-(+)-酒石酸二乙酯 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 69.42h， 生成 (S)-5-[(R)-3-((2S,3S)-3-{2-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-ethyl}-oxiranyl)-1-hydroxy-propyl]-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