(2S,3S,4R)-4-Hydroxy-2,3-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester | 144763-41-7

• 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: (2S,3S,4R)-4-Hydroxy-2,3-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester
• 英文别名: ethyl (2S,3S,4R)-4-hydroxy-2,3-dimethyl-5-oxooxolane-3-carboxylate
• CAS: 144763-41-7
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: ZABINOCDXFHLMX-ATVXKPNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-4-Hydroxy-2,3-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 在 盐酸 、 jones' reagent 、 溶剂黄146 作用下， 反应 4.0h， 生成 3-hydroxy-4,5(R)-dimethyl-2(5H)-furanone
  参考文献：
  名称：

  Enzyme assisted synthesis of (S)-sotolon

  摘要：

  The preparation of enantiomerically enriched sotolon 1 has been studied starting from the racemic precursor 2. Yeast reduction of 2 is diastereoselective, giving access to the corresponding racemic alcohol 3 of anti relative configuration, the acetate of which is resolved into its enantiomers via a lipase catalyzed interesterification with n-butanol. Enantiomerically pure 4 affords (S)-1 of 0.75 ee.

  DOI：

  10.1016/s0040-4039(00)61164-4
• 作为产物：
  描述：

  2,3-dimethyl-4,5-dioxo-tetrahydro-furan-3-carboxylic acid ethyl ester 在 正丁醇 作用下， 以 环己烷 为溶剂， 生成 (2S,3S,4R)-4-Hydroxy-2,3-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enzyme assisted synthesis of (S)-sotolon

  摘要：

  The preparation of enantiomerically enriched sotolon 1 has been studied starting from the racemic precursor 2. Yeast reduction of 2 is diastereoselective, giving access to the corresponding racemic alcohol 3 of anti relative configuration, the acetate of which is resolved into its enantiomers via a lipase catalyzed interesterification with n-butanol. Enantiomerically pure 4 affords (S)-1 of 0.75 ee.

  DOI：

  10.1016/s0040-4039(00)61164-4