Propionic acid (R)-3-benzyloxy-2-hydroxy-propyl ester | 793686-32-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: Propionic acid (R)-3-benzyloxy-2-hydroxy-propyl ester
• 英文别名: [(2R)-2-hydroxy-3-phenylmethoxypropyl] propanoate
• CAS: 793686-32-5
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FTSLSNGZNPSOJO-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Propionic acid (R)-3-benzyloxy-2-hydroxy-propyl ester 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 Pseudomonas cepacia lipase 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 异丙醚 为溶剂， 反应 34.0h， 生成 Propionic acid (S)-2-benzyloxy-1-hydroxymethyl-ethyl ester
  参考文献：
  名称：

  Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)

  摘要：

  A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.07.040
• 作为产物：
  描述：

  1-苄基-2,3-异亚丙基-rac-甘油 在 Amberlyst 15 、 Pseudomonas cepacia lipase 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 71.0h， 生成 Propionic acid (R)-3-benzyloxy-2-hydroxy-propyl ester
  参考文献：
  名称：

  Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)

  摘要：

  A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.07.040

文献信息

• Racemization of α-Alkyl-β-Keto Esters and Enantioselective Total Synthesis of Two C-2′′′Epimers of Plant Glycerolipid Santinol C
  作者：Wen-Ju Wu、Mei-Mei Li、Bo Liu、Yikang Wu

  DOI：10.1002/ejoc.201900467

  日期：2019.6.2

  everyone's surprise, racemization of such optically active methine groups is not as fast as broadly presumed, especially under slightly acidic or neutral conditions. These previously hardly attainable species, including structurally complex ones such as santinol C, now can be readily accessed using Dess–Martin oxidation of the corresponding aldol as the final step of the synthesis along with specially

  可能令所有人惊讶的是，这种旋光性次甲基的外消旋化速度不像人们普遍认为的那样快，尤其是在弱酸性或中性条件下。这些先前难以获得的物种，包括结构复杂的物种，例如三氢萘酚C，现在可以使用相应的羟醛的Dess-Martin氧化作为合成的最后步骤，以及经过特殊设计的便捷分离方案，可以很容易地获得。