ethyl (3S)-4-carbamoyl-3-hydroxybutanoate

• 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: ethyl (3S)-4-carbamoyl-3-hydroxybutanoate
• 英文别名: (S)-3-hydroxyglutaric acid monoamidemonoethyl ester；Ethyl (s)-4-carbamoyl-3-hydroxybutanoate；ethyl (3S)-5-amino-3-hydroxy-5-oxopentanoate
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: JDKCSANQGPFQGM-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-4-carbamoyl-3-hydroxybutanoate 在 吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以90%的产率得到(S)-(+)-4-氰-3-羟基丁酸乙酯
  参考文献：
  名称：

  Absolute configurations of monoesters produced by enzyme catalyzed hydrolysis of diethyl 3-hydroxyglutarate

  摘要：

  Biocatalytic asyminetrizations of diethyl 3-hydroxyglutarate furnish a route to the enantiomers of ethyl 4-cyano-3-hydroxybutanoate. The enantiopreference of different enzymes has been established by chiral chromatography. Conclusive evidence for absolute configurations has been provided by X-ray crystallographic structure determination of co-crystals of the predominant monoester with (R)-phenylethylamine. The predominant enantiopure monoester produced by ammonolysis of diethyl 3-hydroxyglutarate catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) was ethyl (3S)-4-carbamoyl-3-hydroxybutanoate. This was converted to ethyl (3S)-4-cyano-3-hydroxybutanoate in high yield and enantiomeric excess. Growing cells of Acinetohacter lwoffii gave low ee and predominance of the (S)-enantiomer when used for hydrolysis of diethyl 3-hydroxyglutarate as opposed to previous reports. When Novozyni 435 was used for hydrolysis it could be re-used 10 times without loss of activity and selectivity. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.04.007
• 作为产物：
  描述：

  3-羟基戊二酸二乙酯 在 Novozym 435 作用下， 以95%的产率得到ethyl (3S)-4-carbamoyl-3-hydroxybutanoate
  参考文献：
  名称：

  Absolute configurations of monoesters produced by enzyme catalyzed hydrolysis of diethyl 3-hydroxyglutarate

  摘要：

  Biocatalytic asyminetrizations of diethyl 3-hydroxyglutarate furnish a route to the enantiomers of ethyl 4-cyano-3-hydroxybutanoate. The enantiopreference of different enzymes has been established by chiral chromatography. Conclusive evidence for absolute configurations has been provided by X-ray crystallographic structure determination of co-crystals of the predominant monoester with (R)-phenylethylamine. The predominant enantiopure monoester produced by ammonolysis of diethyl 3-hydroxyglutarate catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) was ethyl (3S)-4-carbamoyl-3-hydroxybutanoate. This was converted to ethyl (3S)-4-cyano-3-hydroxybutanoate in high yield and enantiomeric excess. Growing cells of Acinetohacter lwoffii gave low ee and predominance of the (S)-enantiomer when used for hydrolysis of diethyl 3-hydroxyglutarate as opposed to previous reports. When Novozyni 435 was used for hydrolysis it could be re-used 10 times without loss of activity and selectivity. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.04.007

文献信息

• 一种(S)-叔丁基二甲基硅氧基-戊二酸单酰胺 的制备方法
  申请人：浙江新东港药业股份有限公司

  公开号：CN104356155B

  公开（公告）日：2017-01-18

  本发明公开了一种罗素伐他汀中间体(S)‑叔丁基二甲基硅氧基‑戊二酸单酰胺(I)的制备方法，属于医药领域。该方法以化合物（S)‑4‑氰基‑3‑羟基丁酸酯为原料，催化氰成酰胺，在与TBSCl结合，得TBS保护（S)‑叔丁基二甲基硅氧戊二酸单酯单酰胺再与诺维信脂肪酶435水解成（S)‑3‑叔丁基二甲基硅氧基戊二酸单酰胺。本发明方法选择性好，适用于工业生产。
• Absolute configurations of monoesters produced by enzyme catalyzed hydrolysis of diethyl 3-hydroxyglutarate
  作者：Anders Riise Moen、Bård Helge Hoff、Lars Kristian Hansen、Thorleif Anthonsen、Elisabeth Egholm Jacobsen

  DOI：10.1016/j.tetasy.2004.04.007

  日期：2004.5

  Biocatalytic asyminetrizations of diethyl 3-hydroxyglutarate furnish a route to the enantiomers of ethyl 4-cyano-3-hydroxybutanoate. The enantiopreference of different enzymes has been established by chiral chromatography. Conclusive evidence for absolute configurations has been provided by X-ray crystallographic structure determination of co-crystals of the predominant monoester with (R)-phenylethylamine. The predominant enantiopure monoester produced by ammonolysis of diethyl 3-hydroxyglutarate catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) was ethyl (3S)-4-carbamoyl-3-hydroxybutanoate. This was converted to ethyl (3S)-4-cyano-3-hydroxybutanoate in high yield and enantiomeric excess. Growing cells of Acinetohacter lwoffii gave low ee and predominance of the (S)-enantiomer when used for hydrolysis of diethyl 3-hydroxyglutarate as opposed to previous reports. When Novozyni 435 was used for hydrolysis it could be re-used 10 times without loss of activity and selectivity. (C) 2004 Published by Elsevier Ltd.