(S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-pentanedioic acid mono-tert-butyl ester | 264144-31-2

• 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: (S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-pentanedioic acid mono-tert-butyl ester
• CAS: 264144-31-2
• 化学式: C₂₀H₂₅NO₇
• 分子量: 391.421
• InChiKey: URMOEHLLZZVMGC-HACGYAERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110.21
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-pentanedioic acid mono-tert-butyl ester 在 4-二甲氨基吡啶 、 lithium benzyloxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective syntheses of orthogonally protected tricarballylic acid esters

  摘要：

  3(S) and 3(R)-Benzyloxycarbonyl-pentanedioic acid mono-tert-butyl esters (6) were obtained as enantiopure orthogonally protected tricarballylic acid (TCA) esters. These were synthesised by alkylation of the sodium enolate derived from chiral but-3-enoyloxazolidinone imides (3) with tert-butyl bromoacetate; following the hydrolysis to remove the chiral auxiliary, benzyl esterification afforded the 2-allyl succinic acid diesters (4) that were converted to protected TCA esters after oxidation of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02264-9
• 作为产物：
  描述：

  (S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 生成 (S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-pentanedioic acid mono-tert-butyl ester
  参考文献：
  名称：

  Enantioselective syntheses of orthogonally protected tricarballylic acid esters

  摘要：

  3(S) and 3(R)-Benzyloxycarbonyl-pentanedioic acid mono-tert-butyl esters (6) were obtained as enantiopure orthogonally protected tricarballylic acid (TCA) esters. These were synthesised by alkylation of the sodium enolate derived from chiral but-3-enoyloxazolidinone imides (3) with tert-butyl bromoacetate; following the hydrolysis to remove the chiral auxiliary, benzyl esterification afforded the 2-allyl succinic acid diesters (4) that were converted to protected TCA esters after oxidation of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02264-9