methyl <5-<(benzyloxy)methoxy>-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate | 144107-94-8

• 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: methyl <5-<(benzyloxy)methoxy>-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate
• 英文别名: Methyl 2-hydroxy-6-(2-methoxy-2-oxoethyl)-4-(phenylmethoxymethoxy)benzoate
• CAS: 144107-94-8
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: NJZLCQVOCPOKGA-UHFFFAOYSA-N

物化性质

• 沸点：
  521.6±50.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl <5-<(benzyloxy)methoxy>-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate
  参考文献：
  名称：

  An improved synthesis of naphthoate precursors to olivin

  摘要：

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.

  DOI：

  10.1021/jo00050a047
• 作为产物：
  描述：

  苄基氯甲基醚 、 dimethyl 3,5-dihydroxyhomophthalate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以95%的产率得到methyl <5-<(benzyloxy)methoxy>-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate
  参考文献：
  名称：

  An improved synthesis of naphthoate precursors to olivin

  摘要：

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.

  DOI：

  10.1021/jo00050a047

文献信息

• An improved synthesis of naphthoate precursors to olivin
  作者：William R. Roush、Megan Murphy

  DOI：10.1021/jo00050a047

  日期：1992.11

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.