(2R)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]butanedioic acid | 264144-37-8

• 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: (2R)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]butanedioic acid
• CAS: 264144-37-8
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: LDNKHJFTKATVPB-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]butanedioic acid 在 硼烷四氢呋喃络合物 作用下， 生成 tert-butyl (3R)-5-hydroxy-3-(hydroxymethyl)pentanoate
  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 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2R)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]butanedioic 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

• Absolute configuration at the tricarballylic acid moieties of fumonisin B2
  作者：Craig D Boyle、Yoshito Kishi

  DOI：10.1016/0040-4039(95)00852-4

  日期：1995.6

  The configuration at the chiral centers of the two tricarballylic acid moieties of fumonisin B2 is shown to be R. This stereochemistry is opposite to that recently suggested by others for the tricarballylic acid portions of fumonisin B1 and AAL toxin TA.

  在伏马菌素B的两个丙三羧酸部分的手性中心的构型2被示出为[R 。这种立体化学与其他人最近提出的伏马菌素B 1和AAL毒素T A的三碳烯酸部分相反。
• 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.