(2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,6R,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-4,7,10-trimethyl-6,7-bis[(triethylsilyl)oxy]-dodeca-2,11-dienoate | 944943-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,6R,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-4,7,10-trimethyl-6,7-bis[(triethylsilyl)oxy]-dodeca-2,11-dienoate
• 英文别名: [(2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyloxolan-3-yl] (2E,4S,6R,7R,9S,10R)-9-[tert-butyl(dimethyl)silyl]oxy-4,7,10-trimethyl-6,7-bis(triethylsilyloxy)dodeca-2,11-dienoate
• CAS: 944943-00-4
• 化学式: C₄₆H₉₀O₆Si₃
• 分子量: 823.473
• InChiKey: BKEPUAZEHUCKGF-DJCJHXBZSA-N

物化性质

• 沸点：
  699.3±55.0 °C(predicted)
• 密度：
  0.93±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.96
• 重原子数：
  55
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,6R,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-4,7,10-trimethyl-6,7-bis[(triethylsilyl)oxy]-dodeca-2,11-dienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 碳酸氢钠 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 80.0h， 生成 (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E,11E)-(4S,7R,9S,10R)-7,9-dihydroxy-4,7,10-trimethyl-6-oxo-12-phenyldodeca-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：

  3-甲基-3-丁烯-1-醇 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 偶氮二甲酸二异丙酯 、 AD-mix-β 、 2,4,6-三氯苯甲酰氯 、 乙基溴化镁 、 potassium trimethylsilonate 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 108.5h， 生成 (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,6R,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-4,7,10-trimethyl-6,7-bis[(triethylsilyl)oxy]-dodeca-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

文献信息

• Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (<i>E</i>)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes
  作者：Jian Jin、Yile Chen、Yannian Li、Jinlong Wu、Wei-Min Dai

  DOI：10.1021/ol0710360

  日期：2007.6.1

  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.