(R)-4-tert-butoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

• 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: (R)-4-tert-butoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid
• 英文别名: (2R)-2-(2-methoxy-2-oxoethyl)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: DPWIXOZENQSBDV-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  R(+)-alpha-甲基苄胺 、 (R)-4-tert-butoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-O-tert-butyl 1-O-methyl (3R)-3-[[(1R)-1-phenylethyl]carbamoyl]pentanedioate
  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：

  3(R)-benzyloxycarbonylpentanedioic acid mono-tert-butyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-4-tert-butoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid
  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.