(1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-2-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-4-methylcyclopentane-1-carbaldehyde | 1160556-79-5

• 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: (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-2-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-4-methylcyclopentane-1-carbaldehyde
• CAS: 1160556-79-5
• 化学式: C₃₃H₅₄O₅Si
• 分子量: 558.874
• InChiKey: MCNICWSORIJLEG-ANMVPHEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-溴丙烯 、 (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-2-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-4-methylcyclopentane-1-carbaldehyde 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.75h， 以91%的产率得到(1R,2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(1-hydroxy-2-methylallyl)-2-((E)-5-((4-methoxybenzyl)oxy)-2,6,6-trimethylnona-1,8-dien-1-yl)-4-methylcyclopentan-1-ol
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u
• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(hydroxymethyl)-2-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-4-methylcyclopentan-1-ol 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 以81%的产率得到(1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-2-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-4-methylcyclopentane-1-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u