(4E,8E,2S)-1-tert-butyldiphenylsilyloxy-4,8-diethyl-2-methyldecene-4,8-diene | 1243715-47-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4E,8E,2S)-1-tert-butyldiphenylsilyloxy-4,8-diethyl-2-methyldecene-4,8-diene
• CAS: 1243715-47-0
• 化学式: C₃₁H₄₆OSi
• 分子量: 462.791
• InChiKey: MTDBSCISSNDIET-FVYWAPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4E,8E,2S)-1-tert-butyldiphenylsilyloxy-4,8-diethyl-2-methyldecene-4,8-diene 在 Oxone 、 Shi's ketone 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 2.0h， 以57%的产率得到(2S,4R,5R,8R,9R)-1-tert-butyldiphenylsiloxy-4,8-diethyl-2-methyl-4,5;8,9-diepoxydecane
  参考文献：
  名称：

  Intriguing Substrate Tolerance of Epoxide Hydrolase Lsd19 Involved in Biosynthesis of the Ionophore Antibiotic Lasalocid A

  摘要：

  Recently, we reported that the epoxide hydrolase Lsd19, the first enzyme shown to catalyze epoxide-opening cascades, can catalyze the conversion of a putative bisepoxide intermediate to polyether antibiotic lasalocid, which involves energetically disfavored 6-endo-tet cyclization of the epoxy alcohol. Here, we examined the substrate tolerance of Lsd19. Lsd19 accepts various substrate analogues differing in the left segment of lasalocid and epoxide stereochemistry to afford either THF-THP or THF-THF products with excellent regioselectivity.

  DOI：

  10.1021/ol100541e
• 作为产物：
  描述：

  (2E,6E)-3-ethyl-7-iodonona-2,6-diene 、 (R)-3-[(tert-butyl)diphenylsilyloxy]-1-iodo-2-methylpropane 在 叔丁基锂 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 16.0h， 以55%的产率得到(4E,8E,2S)-1-tert-butyldiphenylsilyloxy-4,8-diethyl-2-methyldecene-4,8-diene
  参考文献：
  名称：

  Intriguing Substrate Tolerance of Epoxide Hydrolase Lsd19 Involved in Biosynthesis of the Ionophore Antibiotic Lasalocid A

  摘要：

  Recently, we reported that the epoxide hydrolase Lsd19, the first enzyme shown to catalyze epoxide-opening cascades, can catalyze the conversion of a putative bisepoxide intermediate to polyether antibiotic lasalocid, which involves energetically disfavored 6-endo-tet cyclization of the epoxy alcohol. Here, we examined the substrate tolerance of Lsd19. Lsd19 accepts various substrate analogues differing in the left segment of lasalocid and epoxide stereochemistry to afford either THF-THP or THF-THF products with excellent regioselectivity.

  DOI：

  10.1021/ol100541e