(2R,4R,5S)-2-methyl-2-propyl-4-(triethylsilyl)oxy-5-vinyltetrahydrofuran | 944942-94-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,4R,5S)-2-methyl-2-propyl-4-(triethylsilyl)oxy-5-vinyltetrahydrofuran
• 英文别名: [(2S,3R,5R)-2-ethenyl-5-methyl-5-propyloxolan-3-yl]oxy-triethylsilane
• CAS: 944942-94-3
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: XLTGLKJBBDGKSL-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S)-2-methyl-2-propyl-4-(triethylsilyl)oxy-5-vinyltetrahydrofuran 在 palladium diacetate 4-二甲氨基吡啶 、 potassium phosphate 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 22.25h， 生成 (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,6S,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-6-hydroxy-4,7,10-trimethyl-7-(triethylsilyl)oxydodeca-2,11-dienoate
  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：

  (2S,3R,5R)-2-ethenyl-5-methyl-5-propyloxolan-3-ol 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到(2R,4R,5S)-2-methyl-2-propyl-4-(triethylsilyl)oxy-5-vinyltetrahydrofuran
  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