(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde | 944943-12-8

• 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: (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde
• CAS: 944943-12-8
• 化学式: C₂₉H₅₄O₅Si₂
• 分子量: 538.916
• InChiKey: QBOWCOPKTZCTAX-OWPQXHQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate
  参考文献：
  名称：

  Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (E)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes

  摘要：

  Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.

  DOI：

  10.1021/ol0710360
• 作为产物：
  描述：

  (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde
  参考文献：
  名称：

  Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (E)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes

  摘要：

  Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.

  DOI：

  10.1021/ol0710360