Ethyl (2R,3S,13S)-2,3,13,14-tetrahydroxytetradecanoate 2,3-acetonide | 153915-94-7

• 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: Ethyl (2R,3S,13S)-2,3,13,14-tetrahydroxytetradecanoate 2,3-acetonide
• 英文别名: ethyl (4R,5S)-5-[(10S)-10,11-dihydroxyundecyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 153915-94-7
• 化学式: C₁₉H₃₆O₆
• 分子量: 360.491
• InChiKey: FDUSAPBDDRKWED-YESZJQIVSA-N

物化性质

• 沸点：
  463.5±35.0 °C(predicted)
• 密度：
  1.045±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl (2R,3S,13S)-2,3,13,14-tetrahydroxytetradecanoate 2,3-acetonide 在 偶氮二异丁腈 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 原乙酸三乙酯 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 Ethyl (2R,3S,15R)-13-acetoxy-2,3-dihydroxytetradecanoate acetonide
  参考文献：
  名称：

  A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone

  摘要：

  Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2-dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.

  DOI：

  10.1021/jo00079a024
• 作为产物：
  描述：

  10-undecen-1-ol tosylate 在 AD-mix-α 、 甲基磺酰胺 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 溶剂黄146 、 二甲基亚砜 、 丙酮 、 甲苯 、 paraffin 、 叔丁醇 为溶剂， 反应 32.67h， 生成 Ethyl (2R,3S,13S)-2,3,13,14-tetrahydroxytetradecanoate 2,3-acetonide
  参考文献：
  名称：

  A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone

  摘要：

  Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2-dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.

  DOI：

  10.1021/jo00079a024