methyl 4-(allyloxy)-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 | 144108-04-3

• 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 4-(allyloxy)-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
• 英文别名: methyl 2-[(E,5S,6R)-6-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-6-[(2R,3S)-2-methyl-1,4-dioxaspiro[4.5]decan-3-yl]-2-oxohex-3-enyl]-6-hydroxy-4-prop-2-enoxybenzoate
• CAS: 144108-04-3
• 化学式: C₃₃H₅₀O₉Si
• 分子量: 618.84
• InChiKey: BLQWTQUTNSXKBS-VGYIGPMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4-(allyloxy)-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 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.42h， 生成 methyl 6-(allyloxy)-8,9-bis<(benzyloxy)methoxy>-1-hydroxy-3-<(2'R,3'S,4'R,5'S,6'R)-3'-methoxy-5',6'-(cyclohexylidenedioxy)-4'-<(tert-butyldimethylsilyl)oxy>-2'-vinylheptyl>naphthoate
  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：

  dimethyl 3,5-dihydroxyhomophthalate 在 potassium carbonate 、 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 、 丙酮 、 乙腈 为溶剂， 反应 34.5h， 生成 methyl 4-(allyloxy)-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

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.