Butyric acid (R)-3-benzyloxy-2-hydroxy-propyl ester | 793686-33-6

• 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: Butyric acid (R)-3-benzyloxy-2-hydroxy-propyl ester
• 英文别名: [(2R)-2-hydroxy-3-phenylmethoxypropyl] butanoate
• CAS: 793686-33-6
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: LHUZYXMIAXHMBG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Butyric 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， 生成 (R)-(+)-3-苄氧基-1,2-丙二醇
  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 5.0h， 生成 Butyric 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

• Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)
  作者：Giuseppe Guanti、Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Laura Bondanza、Renata Riva

  DOI：10.1016/j.tetasy.2004.07.040

  日期：2004.9

  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.