methyl (S)-2-tetradecyloxiranecarboxylate | 106974-47-4

• 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: methyl (S)-2-tetradecyloxiranecarboxylate
• 英文别名: methyl (2S)-2-tetradecyloxirane-2-carboxylate
• CAS: 106974-47-4
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: RSSDZUNGAWCFPT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Hydroxy-2-(toluene-4-sulfonyloxymethyl)-hexadecanoic acid methyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 methyl (S)-2-tetradecyloxiranecarboxylate 、 methyl (R)-tetradecyloxiranecarboxylate
  参考文献：
  名称：

  Lipase-Catalyzed Enantioselective Synthesis of Methyl (R)- and (S)-2-Tetradecyloxiranecarboxylate through Sequential Kinetic Resolution

  摘要：

  Among a variety of lipases tested, Pseudomonas fluorescens lipase has been found to induce enantioselective acylation of methyl (R,S)-2-hydroxy-2-(hydroxymethyl)hexadecanoate (3), affording, through sequential kinetic resolution, both enantiomers in good optical yields. Efficiency of the process has been compared to the Sharpless asymmetric dihydroxylation of alkene 2 using (DHQD)(2)PHAL and (DHQ)(2)PHAL as chiral ligands. The (R)- and (S)-3 enantiomers have been cyclized to afford both enantiomers of methyl 2-tetradecyloxiranecarboxylate (1), a potent hypoglycemic agent and inhibitor of long-chain fatty acid oxidation.

  DOI：

  10.1021/jo970109y

文献信息

• Lipase-Catalyzed Enantioselective Synthesis of Methyl (<i>R</i>)- and (<i>S</i>)-2-Tetradecyloxiranecarboxylate through Sequential Kinetic Resolution
  作者：Oscar Jiménez、M. P. Bosch、Angel Guerrero

  DOI：10.1021/jo970109y

  日期：1997.5.1

  Among a variety of lipases tested, Pseudomonas fluorescens lipase has been found to induce enantioselective acylation of methyl (R,S)-2-hydroxy-2-(hydroxymethyl)hexadecanoate (3), affording, through sequential kinetic resolution, both enantiomers in good optical yields. Efficiency of the process has been compared to the Sharpless asymmetric dihydroxylation of alkene 2 using (DHQD)(2)PHAL and (DHQ)(2)PHAL as chiral ligands. The (R)- and (S)-3 enantiomers have been cyclized to afford both enantiomers of methyl 2-tetradecyloxiranecarboxylate (1), a potent hypoglycemic agent and inhibitor of long-chain fatty acid oxidation.