(2S,3S)-ethyl 2-benzamidomethyl-3-hydroxybutyrate | 120236-14-8

• 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: (2S,3S)-ethyl 2-benzamidomethyl-3-hydroxybutyrate
• 英文别名: ethyl (2S,3S)-2-benzamidomethyl-3-hydroxybutanoate；(2S,3S)-2-benzoylaminomethyl-3-hydroxybutyric acid ethyl ester；ethyl (2S,3S)-2-(benzamidomethyl)-3-hydroxybutanoate
• CAS: 120236-14-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: GIRBMFYSMBEDOM-JQWIXIFHSA-N

物化性质

• 沸点：
  484.4±35.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (2S,3S)-ethyl 2-benzamidomethyl-3-hydroxybutyrate 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3S)-3-<(1R)-1-benzoyloxyethyl>azetidin-2-one
  参考文献：
  名称：

  Microbial generation of (2R,3S)- and (2S,3S)-ethyl 2-benzamidomethyl-3-hydroxybutyrate, a key intermediate in the synthesis of (3S,1′R)-3-(1′-hydroxyethyl)azetidin-2-one

  摘要：

  Microbial reduction of the carbonyl group of the substituted acetoacetate esters 3-6 affords directly, or after Ni-Raney desulfurization, the corresponding enantiomerically pure 3S carbinols of variable diastereoisomeric composition. These compounds are transformed into (3S,1'R)-3-(1'-hydroxyethyl)-azetidin-2-one, a useful intermediate in the synthesis of beta-lactam antibiotics.

  DOI：

  10.1039/p19930002247
• 作为产物：
  描述：

  2-(N-苯甲酰胺甲基)-3-酮基丁酸乙酯 在 Gossy ium hirsutum 作用下， 反应 72.0h， 以97%的产率得到(2S,3S)-ethyl 2-benzamidomethyl-3-hydroxybutyrate
  参考文献：
  名称：

  Diastereoselective reduction of β-keto carbonyl compounds by cultured plant cells

  摘要：

  The diastereoselective reduction of beta-keto carbonyl compounds such as 2-benzamidomethyl-3-oxobutanoates and 2-methyl-2-(2-propenyl)cyclopentan-1,3-dione by cultured cells of higher plants was investigated. The reduction of the 2-benzamidomethyl-3-oxobutanoates by Parthenocissus tricitspidata diastercoselectively produced the (2R,3S)-2-benzamidomethyl-3-hydroxybutanoates, whereas the reduction by Gossypium hirsultum gave the (2S,3S)-2-benzimidoinethyl-3-hydroxybutanoates. The (2R,3S)l (2S,3S) predominance in the reduction with Nicotiana tabacum, Glycine max, and Catharan thus roseus was reversed by the change in the structure of the alkoxyl group in the substrate. On the other hand, the reduction of 2-methyl-2-(2-propenyl)cyclopelitan-1,3-dione by P. tricuspidata produced (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopent in-1-one, whereas the reaction by N. tabacum, G. max, C roseus' and G. hirsuatum gave (2S,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.005

文献信息

• WO2006/82054
  申请人：——

  公开号：——

  公开（公告）日：——
• Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts
  作者：Raffaella Gandolfi、Edoardo Cesarotti、Francesco Molinari、Diego Romano、Isabella Rimoldi

  DOI：10.1016/j.tetasy.2009.02.023

  日期：2009.3

  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.
• US4927507A
  申请人：——

  公开号：US4927507A

  公开（公告）日：1990-05-22
• US5064761A
  申请人：——

  公开号：US5064761A

  公开（公告）日：1991-11-12
• US5274188A
  申请人：——

  公开号：US5274188A

  公开（公告）日：1993-12-28