3-[(E)-(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-1-enyl]-isochromen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-[(E)-(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-1-enyl]-isochromen-1-one
• 英文别名: 3-[(E,3S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-4-[(2R,3S)-2-methyl-1,4-dioxaspiro[4.5]decan-3-yl]but-1-enyl]isochromen-1-one
• 化学式: C₂₉H₄₂O₆Si
• 分子量: 514.734
• InChiKey: GJWGAVWFRNQPGH-DGWJGPASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-[(E)-(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-1-enyl]-isochromen-1-one 在 氢氧化钾 作用下， 生成 2-[(E)-(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-2-oxo-hex-3-enyl]-benzoic acid methyl ester
  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：

  (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propionaldehyde 、 Methyl 2-(3-diethoxyphosphoryl-2-oxopropyl)benzoate 在 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， 以90%的产率得到3-[(E)-(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-1-enyl]-isochromen-1-one
  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.