(R)-dimethyl 2-(benzyloxy)succinate | 116233-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-dimethyl 2-(benzyloxy)succinate
• 英文别名: Dimethyl (R)-2-(Benzyloxy)succinate；dimethyl (2R)-2-phenylmethoxybutanedioate
• CAS: 116233-49-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: OJIKXLSNRLSSKS-LLVKDONJSA-N

物化性质

• 沸点：
  349.3±27.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-dimethyl 2-(benzyloxy)succinate 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-(Benzyloxy)butane-1,4-diol
  参考文献：
  名称：

  一种(R)-(+)-1,2,4-丁三醇及其高效合成方法和应用

  摘要：

  一种(R)‑(+)‑1,2,4‑丁三醇及其高效合成方法和应用。本发明属于医药中间体1,2,4‑丁三醇的合成领域。本发明的目的是为了克服现有丁三醇合成路线中除硼操作繁琐、三废量大、能耗高、收率低等技术问题。本发明提供了一种(R)‑(+)‑1,2,4‑丁三醇的合成方法。本发明所述方法通过在苹果酸甲酯的2位羟基上引入保护基，避免了还原反应后处理时的除硼操作，成功实现了(R)‑(+)‑1,2,4‑丁三醇的高效合成。本方法收率高、后处理操作简便，避免了复杂的除硼过程，各步产品易纯化，具有良好的应用价值。

  公开号：

  CN116655449A
• 作为产物：
  描述：

  D-苹果酸二甲酯 、 2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以75%的产率得到(R)-dimethyl 2-(benzyloxy)succinate
  参考文献：
  名称：

  Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway

  摘要：

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.017

文献信息

• Santaniello, Enzo; Ferraboschi, Patrizia; Grisenti, Paride, Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 601 - 605
  作者：Santaniello, Enzo、Ferraboschi, Patrizia、Grisenti, Paride、Aragozzini, Fabrizio、Maconi, Elisabetta

  DOI：——

  日期：——
• Regioselective Transformation of Malic Acid: A Practical Method for the Construction of Enantiomerically Pure Indolizidines
  作者：Peter Gmeiner、Dagmar Junge

  DOI：10.1021/jo00117a052

  日期：1995.6
• WITTMAN, M. D.;KALLMERTEN, J., J. ORG. CHEM., 53,(1988) N 19, C. 4631-4633
  作者：WITTMAN, M. D.、KALLMERTEN, J.

  DOI：——

  日期：——
• Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway
  作者：David Tran、Amy L. Pietersma、Linley R. Schofield、Matthias Rost、Geoffrey B. Jameson、Emily J. Parker

  DOI：10.1016/j.bmcl.2011.09.017

  日期：2011.11

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.