3-benzoylamino-3-phenyl-(ethyl, 2-oxalyl) propenoic acid ethyl ester | 153524-49-3

• 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: 3-benzoylamino-3-phenyl-(ethyl, 2-oxalyl) propenoic acid ethyl ester
• 英文别名: 1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate
• CAS: 153524-49-3
• 化学式: C₂₂H₂₁NO₇
• 分子量: 411.411
• InChiKey: OVICWPAFTKRZRH-UHFFFAOYSA-N

物化性质

• 沸点：
  574.0±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  108.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-benzoylamino-3-phenyl-(ethyl, 2-oxalyl) propenoic acid ethyl ester 在 hansenula polymorpha SC 13865 cells 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 48.5h， 生成 (2R,3S)-3-(苯甲酰基氨基)-2-羟基苯丙酸乙酯
  参考文献：
  名称：

  Microbial synthesis of (2R,3S)-(−)-N-benzoyl-3-phenyl isoserine ethyl ester-a taxol side-chain synthon

  摘要：

  The chiral intermediate (2R,3S)-(-)-N-benzoyl-3-phenyl isoserine ethyl ester 2a, a potential taxol 5 side-chain synthon, was prepared by microbial and enzymatic processes. Taxol 5, is an anticancer compound recently approved by FDA for the treatment of ovarian cancer. The stereoselective reduction of racemic 2-keto-3-(N-benzoylamino)-3-phenylpropionic acid ethyl ester 1 to the corresponding alcohol 2 was carried out using microbial cultures. Among microorganisms evaluated, Hansenula polymorpha SC 13865 and Hansenula fabianii SC 13894 effectively reduced compound 1 to the desired syn diastereomer 2a. Reaction yields of >80% and enantiomeric excesses of >98% were observed for these bioreduction process. About 10-20% of anti diastereomers (2c,2d) were produced during bioreduction.

  DOI：

  10.1016/s0957-4166(00)82256-9
• 作为产物：
  描述：

  L-苯甘氨酸 在 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 3-benzoylamino-3-phenyl-(ethyl, 2-oxalyl) propenoic acid ethyl ester
  参考文献：
  名称：

  Microbial synthesis of (2R,3S)-(−)-N-benzoyl-3-phenyl isoserine ethyl ester-a taxol side-chain synthon

  摘要：

  The chiral intermediate (2R,3S)-(-)-N-benzoyl-3-phenyl isoserine ethyl ester 2a, a potential taxol 5 side-chain synthon, was prepared by microbial and enzymatic processes. Taxol 5, is an anticancer compound recently approved by FDA for the treatment of ovarian cancer. The stereoselective reduction of racemic 2-keto-3-(N-benzoylamino)-3-phenylpropionic acid ethyl ester 1 to the corresponding alcohol 2 was carried out using microbial cultures. Among microorganisms evaluated, Hansenula polymorpha SC 13865 and Hansenula fabianii SC 13894 effectively reduced compound 1 to the desired syn diastereomer 2a. Reaction yields of >80% and enantiomeric excesses of >98% were observed for these bioreduction process. About 10-20% of anti diastereomers (2c,2d) were produced during bioreduction.

  DOI：

  10.1016/s0957-4166(00)82256-9

文献信息

• Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction
  作者：Isabella Rimoldi、Michela Pellizzoni、Giorgio Facchetti、Francesco Molinari、Daniele Zerla、Raffaella Gandolfi

  DOI：10.1016/j.tetasy.2011.11.017

  日期：2011.12

  via asymmetric reduction with transition metal–diphoshine complexes or with whole cells of non-conventional yeasts. Asymmetric hydrogenation was carried out using different approaches: hydrogenation of the tetra-substituted double bond of (E)-1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate 1 with Ir(I)–diphosphine complexes in the presence of TEA, hydrogenation of the carbonyl group

  通过过渡金属-二膦配合物或非常规酵母全细胞的不对称还原，获得了丰富的3-苯甲酰胺基-2-羟基-3-苯基丙酸乙酯（被保护的苯基异丝氨酸）（紫杉醇的手性侧链）。不对称氢化是使用不同的方法：（的四取代的双键的氢化ë）-1-苯甲酰氨基-3-乙氧基-3-氧代-1-苯基丙-1-烯-2-基草酸乙酯1与铱配（I）在TEA存在-diphosphine配合物，外消旋3-苯甲酰氨基-2-氧代-3-苯基丙的羰基的氢化2与钌（II）配合物-diphoshine在路易斯酸和最后一个的存在（E的两步酶促转化）-1-苯甲酰胺基-3-乙氧基-3-氧代-1-苯基丙-1-烯-2-基草酸乙酯1被带有细胞结合酯酶和脱氢酶的酵母全细胞催化。