(S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester | 264144-28-7

• 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)-hex-5-enoic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]hex-5-enoate
• CAS: 264144-28-7
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: DIVLLXCEZQOUCZ-UWWQBHOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 (4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid 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

文献信息

• Enantioselective syntheses of orthogonally protected tricarballylic acid esters
  作者：Nicholas J.S Harmat、Silvia Mangani、Enzo Perrotta、Danilo Giannotti、Rossano Nannicini、Maria Altamura

  DOI：10.1016/s0040-4039(99)02264-9

  日期：2000.2

  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.