methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate | 246523-10-4

• 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: methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate
• 英文别名: methyl (2R,3S)-3-benzamido-2-hydroxy-4-phenylbutanoate
• CAS: 246523-10-4
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: VCQRVASTFNKEIM-JKSUJKDBSA-N

物化性质

• 沸点：
  552.7±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate 在 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 28.0h， 生成 (2S,3s)-3-氨基-2-羟基-4-苯基丁酸
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

  摘要：

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI-272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-alpha-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00249-9
• 作为产物：
  描述：

  (3R,4S)-4-benzyl-3-hydroxy-1-[(S)-1-phenylethyl]azetidin-2-one 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.5h， 生成 methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

  摘要：

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI-272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-alpha-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00249-9

文献信息

• A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates
  作者：Jae-Mok Lee、Hyun-Suk Lim、Kyung-Chang Seo、Sung-Kee Chung

  DOI：10.1016/j.tetasy.2003.10.009

  日期：2003.11

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.
• SAJTO, TEHTSUYUKI;NISIDZAVA, RINDZO;SEHYA, KANDZI;KATO, KUNIMOTO;TAKITA, +
  作者：SAJTO, TEHTSUYUKI、NISIDZAVA, RINDZO、SEHYA, KANDZI、KATO, KUNIMOTO、TAKITA, +

  DOI：——

  日期：——
• Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate
  作者：Hyun-Joon Ha、Young-Gil Ahn、Gwan Sun Lee

  DOI：10.1016/s0957-4166(99)00249-9

  日期：1999.6

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI-272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-alpha-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.