(3S,4S)-4-Hydroxy-tetrahydro-furan-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,4S)-4-Hydroxy-tetrahydro-furan-3-carboxylic acid ethyl ester
• 英文别名: ethyl (3S,4S)-4-hydroxyoxolane-3-carboxylate
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: KCWIESMNMYXYJJ-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙醇 、 (3aR,6aR)-1-(3a,4,6,6a-Tetrahydro-furo[3,4-d]isoxazol-3-yl)-methanol 在 Nickel-Raney 盐酸 、 sodium periodate 、 氢气 、 硼酸 作用下， 生成 (3S,4S)-4-Hydroxy-tetrahydro-furan-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Nitrile oxides in medicinal chemistry. 6. Enzymatic resolution of a set of bicyclic Δ2-isoxazolines

  摘要：

  Chymotrypsin selectively catalyzed the hydrolysis of a series of 3-ethoxycarbonyl-Delta(2)-isoxazolines 1-4, whereas lipase from Pseudomonas cepacia (lipase PS) was remarkably selective in hydrolysing the corresponding 3-hydroxymethyl-Delta(2)-isoxazoline butyrates (5-8). The enantio-preference of chymotrypsin for the first set of compounds is the same as that observed for the lipase PS-cataiyzed hydrolysis of the other series of substrates. The hydrolytic activity of lipase PS for compounds 5-8 was considerably higher than that shown by chymotrypsin for substrates 1-4. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00075-4

文献信息

• Nitrile oxides in medicinal chemistry. 6. Enzymatic resolution of a set of bicyclic Δ2-isoxazolines
  作者：Marco De Amici、Carlo De Micheli、Giacomo Carrea、Sergio Riva

  DOI：10.1016/0957-4166(96)00075-4

  日期：1996.3

  Chymotrypsin selectively catalyzed the hydrolysis of a series of 3-ethoxycarbonyl-Delta(2)-isoxazolines 1-4, whereas lipase from Pseudomonas cepacia (lipase PS) was remarkably selective in hydrolysing the corresponding 3-hydroxymethyl-Delta(2)-isoxazoline butyrates (5-8). The enantio-preference of chymotrypsin for the first set of compounds is the same as that observed for the lipase PS-cataiyzed hydrolysis of the other series of substrates. The hydrolytic activity of lipase PS for compounds 5-8 was considerably higher than that shown by chymotrypsin for substrates 1-4. (C) 1996 Elsevier Science Ltd