(2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanoic acid | 195510-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanoic acid
• 英文别名: (2R,3S)-3-N,N-dibenzylamino-2-hydroxy-4-phenylbutyric acid；threo-3-N,N-dibenzylamino-2-hydroxy-4-phenylbutyric acid
• CAS: 195510-33-9
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: TUFCXHVVCOIDOK-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanoic acid 在 20 percent palladium hydroxide /C 氢气 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到(2R,3S)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: a route to enantiopure β-amino-α-hydroxy acids

  摘要：

  Chiral alpha -dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-beta -dibenzylamino-alpha -hydroxy-cyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure beta -amino-alpha -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00044-1
• 作为产物：
  描述：

  苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 盐酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 14.0h， 生成 (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanoic acid
  参考文献：
  名称：

  Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: a route to enantiopure β-amino-α-hydroxy acids

  摘要：

  Chiral alpha -dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-beta -dibenzylamino-alpha -hydroxy-cyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure beta -amino-alpha -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00044-1

文献信息

• Process for producing norstatin derivatives
  申请人：Kaneka Corporation

  公开号：US06281379B1

  公开（公告）日：2001-08-28

  This invention to provide a process for producing an optically active threo-phenylnorstatin derivative which does not require a toxic cyanating agent or a costly reagent, or a complicated procedure, and can be practiced on a commercial scale. This invention is directed to a process for producing a &bgr;-amino-&agr;-hydroxy acid derivative which comprises treating either a &ggr;-amino-&bgr;-keto sulfoxide derivative with a halogenating agent to produce a &ggr;-amino-&agr;-halo-&bgr;-keto sulfoxide derivative, treating the same with an acid and an alcohol to produce a &bgr;-amino-&agr;-keto ester derivative or &bgr;-amino-&agr;-keto acid derivative, and followed by reducing.

  这项发明提供了一种生产光学活性的threo-phenylnorstatin衍生物的方法，该方法不需要有毒的氰化剂或昂贵的试剂，也不需要复杂的程序，可以在商业规模上实施。这项发明涉及一种生产β-氨基-α-羟基酸衍生物的方法，包括用卤化剂处理γ-氨基-β-酮亚砜衍生物以产生γ-氨基-α-卤-β-酮亚砜衍生物，再用酸和醇处理相同物质以产生β-氨基-α-酮酯衍生物或β-氨基-α-酮酸衍生物，最后进行还原。
• Process for producing erythro-3-amino-2-hydroxybutyric acid derivatives
  申请人：Daiso Co., Ltd.

  公开号：US06365754B1

  公开（公告）日：2002-04-02

  The present invention relates to a process for reacting &agr;-aminoaldehyde derivatives having a sterically bulky amino group which are commercially available with a metal cyanide in the presence of an acid chloride, an acid anhydride or the like to synthesize 3-amino-2-hydroxybutyronitrile derivatives in high yields and high erythro selectivity. When optically active &agr;-aminoaldehyde derivatives are used, racemization hardly occurs during the reaction, and the desired products are obtained in high optical purity.

  本发明涉及一种方法，用于将具有立体位阻氨基团的α-氨基醛衍生物与金属氰化物在酸氯化物、酸酐或类似物的存在下反应，以高产率和高红细胞选择性合成3-氨基-2-羟基丁腈衍生物。当使用光学活性的α-氨基醛衍生物时，在反应过程中几乎不会发生外消旋，所以可以获得高光学纯度的期望产物。
• Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors
  作者：Kwang Seob Lee、Seon Hee Seo、Yong Ha Lee、Ha Dong Kim、Moon Ho Son、Bong Young Chung、Jae Yeol Lee、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.bmcl.2005.03.095

  日期：2005.6

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: a route to enantiopure β-amino-α-hydroxy acids
  作者：José M. Andrés、Marı́a A. Martı́nez、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0957-4166(01)00044-1

  日期：2001.2

  Chiral alpha -dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-beta -dibenzylamino-alpha -hydroxy-cyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure beta -amino-alpha -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.