(2S,3S)-3-hydroxy-N-phthaloylphenylalanine methyl ester | 33551-74-5

• 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)-3-hydroxy-N-phthaloylphenylalanine methyl ester
• 英文别名: methyl 2-(1,3-dioxoisoindol-2-yl)-3-hydroxy-3-phenylpropanoate
• CAS: 33551-74-5
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: WKELEKDLRJUBCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (S)-methyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 四氯化碳 、 水 、 丙酮 为溶剂， 生成 (2S,3S)-3-hydroxy-N-phthaloylphenylalanine methyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives

  摘要：

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.

  DOI：

  10.1016/s0040-4020(01)85256-x

文献信息

• Highly Diastereo- and Enantioselective Access to <i>syn</i>-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation
  作者：Bin Lu、Xiaoyu Wu、Chengyang Li、Guangni Ding、Wanfang Li、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.joc.8b03106

  日期：2019.3.15

  asymmetric hydrogenation was realized at 70 °C under 50 atm of hydrogen, affording syn α-amido β-hydroxy esters in high yields (up to 96%) with high reactivity (TON up to 940) and diastereo- and enantioselectivities (up to 99:1 dr, 98% ee). These hydrogenation products provide valuable chiral synthons in many natural products and pharmaceuticals. Gram-scale DKR asymmetric hydrogenation (DKR-AH) was

  通过Ru-二膦催化的不对称氢化在70°C和50 atm氢气下实现外消旋芳基α-氨基β-酮酸酯的动态动力学拆分（DKR），提供高收率的合成α-酰胺基β-羟基酯（高达96％）具有高反应活性（TON高达940）以及非对映和对映选择性（高达99：1 dr，98％ee）。这些氢化产物在许多天然产物和药物中提供了有价值的手性合成子。还进行了克级DKR不对称氢化（DKR-AH），并保留了反应活性和立体选择性，从而揭示了该方法的合成效用。
• Synthesis of homochiral hydroxy-α-amino acid derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Wui Tan Eng、Edward R.T. Tiekink

  DOI：10.1016/s0040-4039(00)97242-3

  日期：1990.1
• Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives
  作者：Craig A. Hutton

  DOI：10.1016/s0040-4039(97)01314-2

  日期：1997.8

  The degree of stereoconvergence in the synthesis of beta-hydroxyarylalanine derivatives from the corresponding beta-bromoarylalanine derivatives is governed by the electronic nature of the aryl substituents, and controlled by facially selective stabilisation of the benzylic cation through the neighbouring ester moiety. introduction of electron donating aryl substituents results in a decrease in selectivity, whereas electron withdrawing substituents induce an increase in selectivity for the threo-beta-hydroxyarylalanine diastereomer. (C) 1997 Elsevier Science Ltd.