ethyl (4R,5R)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2E)-heptenoate | 700870-74-2

• 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: ethyl (4R,5R)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2E)-heptenoate
• 英文别名: ethyl (E,4R,5R)-5-formyloxy-4-[(4-methoxyphenyl)methoxy]-7-phenylhept-2-enoate
• CAS: 700870-74-2
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: WWSBWXMHXNEWGX-LBBXHWODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 ethyl (4R,5R)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2E)-heptenoate 在 potassium carbonate 作用下， 反应 1.0h， 以95%的产率得到methyl (4R,5R)-4-(4-methoxybenzyloxy)-5-hydroxy-7-phenyl-(2E)-heptenoate
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-5-((Z)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole 在 palladium on activated charcoal sodium periodate 、 硫酸 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 ethyl (4R,5R)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2E)-heptenoate
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n