(-)-(4R,5S)-4-tetradecanoyl-5-((E)-hept-1-enyl)tetrahydrofuran-2-one | 320779-60-0

• 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: (-)-(4R,5S)-4-tetradecanoyl-5-((E)-hept-1-enyl)tetrahydrofuran-2-one
• 英文别名: [(2S,3R)-2-[(E)-hept-1-enyl]-5-oxooxolan-3-yl] tetradecanoate
• CAS: 320779-60-0
• 化学式: C₂₅H₄₄O₄
• 分子量: 408.622
• InChiKey: ZEQXBISHMUHELT-ABZSSTOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(4R,5S)-4-tetradecanoyl-5-((E)-hept-1-enyl)tetrahydrofuran-2-one 在 臭氧 、 dimethyl sulfide borane 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以40%的产率得到(+)-(4R,5S)-4-tetradecanoyl-5-hydroxymethyltetrahydrofuran-2-one
  参考文献：
  名称：

  A Novel Stereoselective Access to Substituted l-2-Deoxypentono-1,4-lactones and l-2-Deoxypentoses

  摘要：

  A stereoselective method to L-2-deoxypentose or L-2-deoxy-pentono-1,4-lactone units was developed employing the (S)-Hydroxynitrile lyase from Hevea brasiliensis. Additionally a diastereoselective reduction using either (D)- or (L)-tartaric acid in conjuction with sodium borohydride had been applied to control the ultimate stereochemistry of the bioactive compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00871-1
• 作为产物：
  描述：

  (+)-(2S,3E)-2-[(tert-butyldiphenylsilyl)oxy]non-3-enenitrile 在 吡啶 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 L-酒石酸 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 85.5h， 生成 (-)-(4R,5S)-4-tetradecanoyl-5-((E)-hept-1-enyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  A Novel Stereoselective Access to Substituted l-2-Deoxypentono-1,4-lactones and l-2-Deoxypentoses

  摘要：

  A stereoselective method to L-2-deoxypentose or L-2-deoxy-pentono-1,4-lactone units was developed employing the (S)-Hydroxynitrile lyase from Hevea brasiliensis. Additionally a diastereoselective reduction using either (D)- or (L)-tartaric acid in conjuction with sodium borohydride had been applied to control the ultimate stereochemistry of the bioactive compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00871-1

文献信息

• A Novel Stereoselective Access to Substituted l-2-Deoxypentono-1,4-lactones and l-2-Deoxypentoses
  作者：Dean V. Johnson、Roland Fischer、Herfried Griengl

  DOI：10.1016/s0040-4020(00)00871-1

  日期：2000.11

  A stereoselective method to L-2-deoxypentose or L-2-deoxy-pentono-1,4-lactone units was developed employing the (S)-Hydroxynitrile lyase from Hevea brasiliensis. Additionally a diastereoselective reduction using either (D)- or (L)-tartaric acid in conjuction with sodium borohydride had been applied to control the ultimate stereochemistry of the bioactive compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.