methyl 4-(allyloxy)-6-<(4'R,5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxo-4'-vinylnonyl>-2-hydroxybenzoate

• 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-<(4'R,5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxo-4'-vinylnonyl>-2-hydroxybenzoate
• 英文别名: methyl 2-[(4R)-4-[(1S,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methoxy-2-[(2R,3S)-2-methyl-1,4-dioxaspiro[4.5]decan-3-yl]ethyl]-2-oxohex-5-enyl]-6-hydroxy-4-prop-2-enoxybenzoate
• 化学式: C₃₅H₅₄O₉Si
• 分子量: 646.894
• InChiKey: ASXRQPGLNHTCAK-BNHYENTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  dimethyl <3-<5'-(allyloxy)-2'-carbomethoxy-3'-hydroxyphenyl>-2-oxopropyl>phosphonate 在 三甲基氯硅烷 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 25.33h， 生成 methyl 4-(allyloxy)-6-<(4'R,5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxo-4'-vinylnonyl>-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