methyl (2S,3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-2-hydroxy-2-methyl-5-phenylpentanoate | 184844-16-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2S,3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-2-hydroxy-2-methyl-5-phenylpentanoate
• CAS: 184844-16-4
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: PFUOBCVEUBACRG-SKPFHBQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-2-hydroxy-2-methyl-5-phenylpentanoate 在 lithium hydroxide 、 二氯特诺 、 双氧水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Structure-based design and synthesis of a series of hydroxamic acids with a quaternary-hydroxy group in P1 as inhibitors of matrix metalloproteinases

  摘要：

  Examination of the S1 area of the active site of pro-stromelysin has led us to the design of novel and potent inhibitors of matrix metalloproteinases containing constrained quaternary-hydroxy group at pi. The synthesis and biological activity of these compounds with variations at P1', P2', and P3' will be described. (C) 1998 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00125-5
• 作为产物：
  描述：

  丙酮酸甲酯 、 (S)-4-benzyl-3-(3-phenylbutanoyl)oxazolidin-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl (2S,3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-2-hydroxy-2-methyl-5-phenylpentanoate 、 (2R,3R)-3-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-2-hydroxy-2-methyl-5-phenyl-pentanoic acid methyl ester
  参考文献：
  名称：

  手性酰亚胺烯酸酯与α-酮酯的不对称反应

  摘要：

  提出了一种合成各种2-羟基-2，3-三取代的琥珀酸酯（I）的方法。合成是通过Evans手性酰亚胺的锂，硼或钛的烯醇化物与α-酮酸酯的不对称反应实现的。

  DOI：

  10.1016/0040-4039(96)01843-6

文献信息

• Asymmetric reactions of chiral imide enolates with α-keto esters
  作者：Irina C. Jacobson、G.Prabhakar Reddy

  DOI：10.1016/0040-4039(96)01843-6

  日期：1996.11

  A method for the synthesis of a variety of 2-hydroxy-2,3-trisubstituted succinates (I) is presented. The synthesis is achieved by the asymmetric reactions of lithium, boron or titanium enolates of Evans' chiral imides with α-keto esters.

  提出了一种合成各种2-羟基-2，3-三取代的琥珀酸酯（I）的方法。合成是通过Evans手性酰亚胺的锂，硼或钛的烯醇化物与α-酮酸酯的不对称反应实现的。
• Structure-based design and synthesis of a series of hydroxamic acids with a quaternary-hydroxy group in P1 as inhibitors of matrix metalloproteinases
  作者：Irina C. Jacobson、Prabhakar G. Reddy、Zelda R. Wasserman、Karl D. Hardman、Maryanne B. Covington、Elizabeth C. Arner、Robert A. Copeland、Carl P. Decicco、Ronald L. Magolda

  DOI：10.1016/s0960-894x(98)00125-5

  日期：1998.4

  Examination of the S1 area of the active site of pro-stromelysin has led us to the design of novel and potent inhibitors of matrix metalloproteinases containing constrained quaternary-hydroxy group at pi. The synthesis and biological activity of these compounds with variations at P1', P2', and P3' will be described. (C) 1998 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.