Butyric acid (R)-2-methyl-3-oxo-isoxazolidin-5-ylmethyl ester | 140384-86-7

• 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: Butyric acid (R)-2-methyl-3-oxo-isoxazolidin-5-ylmethyl ester
• 英文别名: [(5R)-2-methyl-3-oxo-1,2-oxazolidin-5-yl]methyl butanoate
• CAS: 140384-86-7
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: SXZDBRMDMTYDBW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-2-methyl-5-(hydroxymethyl)isoxazolidin-3-one butyrate 在 Lipase PS potassium phosphate buffer 作用下， 以 丙酮 为溶剂， 生成 (5R)-2-Methyl-5-hydroxymethyl-3-oxoisoxazolidine 、 (5S)-2-Methyl-5-hydroxymethyl-3-oxoisoxazolidine 、 Butyric acid (R)-2-methyl-3-oxo-isoxazolidin-5-ylmethyl ester 、 Butyric acid (S)-2-methyl-3-oxo-isoxazolidin-5-ylmethyl ester
  参考文献：
  名称：

  Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives

  摘要：

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.

  DOI：

  10.1021/jo00036a013

文献信息

• Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives
  作者：Marco De Amici、Paolo Magri、Carlo De Micheli、Francesca Cateni、Roberto Bovara、Giacomo Carrea、Sergio Riva、Gianluigi Casalone

  DOI：10.1021/jo00036a013

  日期：1992.5

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.