ethyl 2-(benzamidomethyl)-3-hydroxybutanoate | 903529-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(benzamidomethyl)-3-hydroxybutanoate
• 英文别名: 2-benzoylaminomethyl-3-hydroxybutyric acid ethyl ester
• CAS: 903529-16-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: GIRBMFYSMBEDOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(N-苯甲酰胺甲基)-3-酮基丁酸乙酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 ethyl 2-(benzamidomethyl)-3-hydroxybutanoate
  参考文献：
  名称：

  Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts

  摘要：

  The stereoselective reduction of ethyl 2-(benzamidomethyl)-3-oxobutanoate 1 using yeasts was investigated among a restricted number (12) of yeasts. Kluyveromyces marxianus var. lactis CL69 diastereoselectively produced (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2. whereas Pichia glucozyma CBS 5766 gave (2S,3S)-2 as the major stereoisomer. The biotransformations were independently optimized for minimizing by-product formation and maximizing the diastereoselectivity. Under optimized conditions, K. marxianus var. lactis CL 69 gave the (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2 with ee > 99% and de = 98%, while P. glucozyma CBS 5766 allowed for the production of (2S,3S)-2 with ee > 99% and de = 86%. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.023

文献信息

• Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation
  作者：Xiaoming Li、Xiaoming Tao、Xin Ma、Wanfang Li、Mengmeng Zhao、Xiaomin Xie、Tahar Ayad、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1016/j.tet.2013.05.136

  日期：2013.8

  higher activity and selectivity than the corresponding [Ru(cymene)I2]2–Sunphos. In situ generated catalyst could be used for this transformation. Asymmetric hydrogenation of a series of β′-keto-β-amino esters derivatives using Ru–Sunphos complexes via dynamic kinetic resolution led to the corresponding β′-hydroxy-β-amino esters with ee up to 99.6% and de up to 98.8% (S/C=1000).

  通过深入研究反应条件，开发了一种方便的对映选择性合成β'-羟基-β-氨基酯的方法。发现二氯甲烷（DCM）/ 2,2,2-三氟乙醇（TFE）和1,2-二氯乙烷（DCE）/ TFE组合是该反应的合适助溶剂。在这种混合溶剂体系中，[Ru（cymene ）Cl 2 ] 2 -Sunphos的活性和选择性都比相应的[Ru（cymene）I 2 ] 2高。–Sunphos。原位产生的催化剂可用于该转化。使用Ru-Sunphos配合物通过动态动力学拆分对一系列β'-酮-β-氨基酯衍生物进行不对称加氢，导致相应的β'-羟基-β-氨基酯的ee高达99.6％，de高达98.8％ （S / C＝ 1000）。
• METHOD FOR PRODUCING OPTICALLY ACTIVE 2-(N-SUBSTITUTED AMINOMETHYL)-3-HYDROXYBUTYRIC ACID ESTER
  申请人：Yasohara Yoshihiko

  公开号：US20090104671A1

  公开（公告）日：2009-04-23

  The present invention relates to a method for producing optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid esters wherein a 2-(N-substituted aminomethyl)-3-oxobutyric acid ester is treated with an enzyme source capable of stereoselectively reducing said ester to the corresponding optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid ester having the (2S,3R) configuration. The present invention provides an efficient method for industrially producing optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid esters, in particular such compounds having the (2S,3R) configuration, which are useful as intermediates for the production of medicinal compounds, among others.

  本发明涉及一种制备光学活性的2-(N-取代氨甲基)-3-羟基丁酸酯的方法，其中将2-(N-取代氨甲基)-3-氧代丁酸酯与能够立体选择性还原所述酯的酶源处理，以得到相应的具有(2S,3R)构型的光学活性的2-(N-取代氨甲基)-3-羟基丁酸酯。本发明提供了一种高效的工业制备光学活性的2-(N-取代氨甲基)-3-羟基丁酸酯的方法，特别是具有(2S,3R)构型的化合物，这些化合物可用作药物化合物的中间体等。
• Method for producing optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid ester
  申请人：KANEKA CORPORATION

  公开号：EP2357248A1

  公开（公告）日：2011-08-17

  The present invention relates to a method for producing optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid esters wherein a 2-(N-substituted aminomethyl)-3-oxobutyric acid ester is treated with an enzyme source capable of stereoselectively reducing said ester to the corresponding optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid ester having the (2S,3R) configuration. The present invention provides an efficient method for industrially producing optically active 2-(N-substituted aminomethyl)-3-hydroxybutyric acid esters, in particular such compounds having the (2S,3R) configuration, which are useful as intermediates for the production of medicinal compounds, among others.

  本发明涉及一种生产光学活性 2-(N-取代氨甲基)-3-羟基丁酸酯的方法。 本发明涉及一种生产光学活性 2-(N-取代氨基甲基)-3-羟基丁酸酯的方法，其中 2-(N-取代氨基甲基)-3-氧代丁酸酯用一种酶源处理，该酶源能够立体选择性地将所述酯还原为具有 (2S,3R) 构型的相应光学活性 2-(N-取代氨基甲基)-3-羟基丁酸酯。本发明提供了一种工业化生产光学活性 2-(N-取代氨甲基)-3-羟基丁酸酯的有效方法。 氨基甲基）-3-羟基丁酸酯，特别是具有 (2S,3R) 构型的此类化合物的有效方法，这些化合物可用作生产药用化合物等的中间体。
• DIOPHEP, a chiral diastereoisomeric bisphosphine ligand: synthesis and applications in asymmetric hydrogenations
  作者：Edoardo Cesarotti、Giorgio Abbiati、Elisabetta Rossi、Paola Spalluto、Isabella Rimoldi

  DOI：10.1016/j.tetasy.2008.07.009

  日期：2008.7

  Novel optically active diphosphine ligands, known as DIOPHEP, have been designed and synthesized starting from a derivative of tartaric acid. The ligands conjugate the sp(3) chirality of the precursor of DIOP with the atropisomeric chirality of a biaryl scaffold. The stereorecognition abilities of DIOPHEP-Ru complex catalysts have been investigated in the asymmetric catalytic hydrogenation of some standard substrates suggesting a close relationship between dihedral angles and enantioselectivity. (C) 2008 Published by Elsevier Ltd.
• US4927507A
  申请人：——

  公开号：US4927507A

  公开（公告）日：1990-05-22