trimethyl 2-[(carboxymethyl)oxy]succinate | 51980-33-7

• 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: trimethyl 2-[(carboxymethyl)oxy]succinate
• 英文别名: trimethyl (carboxymethoxy)succinate；Carboxymethyl-oxybernsteinsaeuretrimethylester；Dimethyl 2-(2-methoxy-2-oxoethoxy)butanedioate
• CAS: 51980-33-7
• 化学式: C₉H₁₄O₇
• 分子量: 234.206
• InChiKey: OBURGFBAVZIWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trimethyl 2-[(carboxymethyl)oxy]succinate 在 exchange resin AG 50W-X₈ 作用下， 以 水 为溶剂， 以98%的产率得到2-(羧甲基氧基)丁二酸
  参考文献：
  名称：

  Vijverberg, C. A. M.; Peters, J. A.; Bovee, W. M. M. J., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 5, p. 255 - 263

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 羧基甲氧基琥珀酸钠盐 在 硫酸 作用下， 反应 5.0h， 以14.5 g的产率得到trimethyl 2-[(carboxymethyl)oxy]succinate
  参考文献：
  名称：

  Use of enantio-, chemo- and regioselectivity of acylase I. Resolution of polycarboxylic acid esters

  摘要：

  Acylase I was used to catalyze the enantioselective butanolysis of trimethyl 2-[(carboxymethyl)oxy]succinate (E=30) and N-carboxymethylaspartate (E=9) exclusively at the most sterically hindered of the three ester group's (the position alpha to the asymmetric centre). Gram-scale resolution allowed the preparation of the less reactive trimethyl (S)-2-[(carboxymethyl)oxy]succinate (96% e.e.), that of the (R)-butyldimethyl regioisomer (78% e.e.) at 55% conversion and finally the preparation of the corresponding trisodium carboxylate by saponification. Acylase I was shown to transform (+/-)-methyl N-acetylmethionine and (+/-)-valine to the corresponding (S)-amino acids through ester hydrolysis-N-acetyl transfer sequence with absolute chemo- and enantioselectivity. Butanolysis of methyl N-acetylmethionine stopped in the formation of the butyl ester (E=12), the valine derivative being totally unreactive. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00362-7

文献信息

• US3997698A
  申请人：——

  公开号：US3997698A

  公开（公告）日：1976-12-14
• US3959373A
  申请人：——

  公开号：US3959373A

  公开（公告）日：1976-05-25
• Use of enantio-, chemo- and regioselectivity of acylase I. Resolution of polycarboxylic acid esters
  作者：Arto Liljeblad、Reijo Aksela、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(01)00362-7

  日期：2001.8

  Acylase I was used to catalyze the enantioselective butanolysis of trimethyl 2-[(carboxymethyl)oxy]succinate (E=30) and N-carboxymethylaspartate (E=9) exclusively at the most sterically hindered of the three ester group's (the position alpha to the asymmetric centre). Gram-scale resolution allowed the preparation of the less reactive trimethyl (S)-2-[(carboxymethyl)oxy]succinate (96% e.e.), that of the (R)-butyldimethyl regioisomer (78% e.e.) at 55% conversion and finally the preparation of the corresponding trisodium carboxylate by saponification. Acylase I was shown to transform (+/-)-methyl N-acetylmethionine and (+/-)-valine to the corresponding (S)-amino acids through ester hydrolysis-N-acetyl transfer sequence with absolute chemo- and enantioselectivity. Butanolysis of methyl N-acetylmethionine stopped in the formation of the butyl ester (E=12), the valine derivative being totally unreactive. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Vijverberg, C. A. M.; Peters, J. A.; Bovee, W. M. M. J., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 5, p. 255 - 263
  作者：Vijverberg, C. A. M.、Peters, J. A.、Bovee, W. M. M. J.、Vroon, H.、Kieboom, A. P. G.、Bekkum, H. van

  DOI：——

  日期：——