S-tricarballylic acid bis-t-butyl ester | 162038-12-2

• 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: S-tricarballylic acid bis-t-butyl ester
• 英文别名: (S)-di-tert-butyl carboxymethylsuccinate；(3S)-5-[(2-methylpropan-2-yl)oxy]-3-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopentanoic acid
• CAS: 162038-12-2
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: MCAGTJSUTVTPPE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  S-tricarballylic acid bis-t-butyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 dimethyl (2S)-2-[2-[[(1R)-1-naphthalen-1-ylethyl]amino]-2-oxoethyl]butanedioate
  参考文献：
  名称：

  An NMR method for determination of configuration of β-substituted carboxylic acids

  摘要：

  The absolute configuration of the stereogenic center at the beta-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of beta-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00163-5
• 作为产物：
  描述：

  3-tert-Butoxycarbonyl-pentanedioic acid benzyl ester tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以30%的产率得到S-tricarballylic acid bis-t-butyl ester
  参考文献：
  名称：

  高效，立体选择性合成J-104,118，一种新型，有效的鲨烯合酶抑制剂

  摘要：

  J-104,118，一种新型和有效的角鲨烯合酶抑制剂，是立体选择性合成的。通过Sharpless不对称二羟基化反应作为关键反应有效地合成了手性胺1。

  DOI：

  10.1016/0040-4039(95)01542-6

文献信息

• Efficient and stereoselective synthesis of J-104,118, a novel, potent inhibitor of squalene synthase
  作者：Yoshikazu Iwasawa、Katsumasa Nonoshita、Koji Tomimoto

  DOI：10.1016/0040-4039(95)01542-6

  日期：1995.10

  J-104,118, a novel and potent inhibitor of squalene synthase, was synthesized stereoselectively. The chiral amine 1 was efficiently synthesized by Sharpless asymmetric dihydroxylation as a key reaction.

  J-104,118，一种新型和有效的角鲨烯合酶抑制剂，是立体选择性合成的。通过Sharpless不对称二羟基化反应作为关键反应有效地合成了手性胺1。
• SUBSTITUTED AMIDE DERIVATIVE
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0776884B1

  公开（公告）日：2000-01-05
• Stereoselective synthesis of J-104,118 and J-104,123, novel, potent inhibitors of squalene synthase
  作者：Yoshikazu Iwasawa、Jun Shibata、Katsumasa Nonoshita、Sachie Arai、Hitoshi Masaki、Koji Tomimoto

  DOI：10.1016/0040-4020(96)00850-2

  日期：1996.10

  A novel class of squalene synthase inhibitors (J-104,118 and J-104,123) were synthesized efficiently. An amine intermediate 1 was synthesized using two distinct methods. First, the racemic amine 1 was synthesized diastereoselectively using a key reaction consisting of the stereo-controlled reduction of the ketone 7 by L-Selectride®. Second, the optically active amine 1 was synthesized efficiently and

  有效合成了新型的角鲨烯合酶抑制剂（J-104,118和J-104,123）。使用两种不同的方法合成了胺中间体1。首先，外消旋胺1是通过关键反应非对映选择性合成的，该关键反应由L-Selectride®对酮7进行立体控制的还原反应组成。其次，使用Sharpless二羟基化作为关键反应，高效地和对映选择性地合成了光学活性胺1。从可商购的（R）-3-羟基丁酸甲酯开始开发了一种立体控制的合成J-104,123的方法。
• An NMR method for determination of configuration of β-substituted carboxylic acids
  作者：Thomas R Hoye、Abdel-Sattar S Hamad、Dmitry O Koltun、Manomi A Tennakoon

  DOI：10.1016/s0040-4039(00)00163-5

  日期：2000.4

  The absolute configuration of the stereogenic center at the beta-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of beta-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration. (C) 2000 Elsevier Science Ltd. All rights reserved.