Ethyl (2S,3R)-2,3-epoxydecanoate | 161346-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl (2S,3R)-2,3-epoxydecanoate
• 英文别名: ethyl (2S,3R)-3-heptyloxirane-2-carboxylate
• CAS: 161346-13-0
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: NDISNNKAFSHFFO-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl (2S,3R)-2,3-epoxydecanoate 在 titanium(IV) isopropylate 、 盐酸 、 sodium hydroxide 、 叠氮化锂 、 N,N-二异丙基乙胺 、 焦碳酸二乙酯 作用下， 以 乙醇 为溶剂， 反应 37.0h， 生成 (S)-2-[(S)-2-({(S)-2-[(S)-2-((2S,3S)-3-Azido-2-hydroxy-decanoylamino)-propionylamino]-3-methyl-butyryl}-methyl-amino)-3-(4-benzyloxy-phenyl)-propionylamino]-3-(4-benzyloxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

  摘要：

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.

  DOI：

  10.1016/s0040-4020(01)89431-x
• 作为产物：
  描述：

  ethyl (2S,3R)-2-bromo-3-hydroxydecanoate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到Ethyl (2S,3R)-2,3-epoxydecanoate
  参考文献：
  名称：

  Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

  摘要：

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.

  DOI：

  10.1016/s0040-4020(01)89431-x

文献信息

• Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters
  作者：Sadao Tsuboi、Hiroyuki Furutani、Mohammad Hafeez Ansari、Takashi Sakai、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00054a036

  日期：1993.1

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.