(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol | 859436-76-3

• 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: (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol
• 英文别名: (2R,3R)-1-tert-butyldiphenylsilyloxy-3,7-dimethyl-6-octene-2,3-diol
• CAS: 859436-76-3
• 化学式: C₂₆H₃₈O₃Si
• 分子量: 426.671
• InChiKey: APGKNZOLQZYBNA-AOYPEHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (R)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  Enzyme-assisted synthesis of (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle, and its (R)-enantiomer

  摘要：

  (S)-1,3-Dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle (Leptinotarsa decemlineata), and its (R)-isomer were synthesized by employing lipase-catalyzed asymmetric acetylation of (+/-)-2,3-epoxynerol as the key step. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.030
• 作为产物：
  描述：

  (2S,3R)-3,7-dimethyl-2,3-epoxy-6-octenyl acetate 在 4-二甲氨基吡啶 、 高氯酸 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol
  参考文献：
  名称：

  Enzyme-assisted synthesis of (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle, and its (R)-enantiomer

  摘要：

  (S)-1,3-Dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle (Leptinotarsa decemlineata), and its (R)-isomer were synthesized by employing lipase-catalyzed asymmetric acetylation of (+/-)-2,3-epoxynerol as the key step. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.030

文献信息

• Organic Synthesis in Pheromone Science
  作者：Kenji Mori

  DOI：10.3390/10091023

  日期：——

  Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are summarized to emphasize biodiversity as revealed in pheromone perception.

  给出了例子来说明化学和/或酶促不对称反应在合成宽角面粉甲虫、跳虫、黑加仑茎切割虫和科罗拉多土豆甲虫的新信息素中的应用。总结了信息素中立体化学与生物活性之间的关系，以强调在信息素感知中揭示的生物多样性。
• A protecting group-free synthesis of the Colorado potato beetle pheromone
  作者：Zhongtao Wu、Manuel Jäger、Jeffrey Buter、Adriaan J Minnaard

  DOI：10.3762/bjoc.9.273

  日期：——

  A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]₂OTf₂. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.

  基于Sharpless不对称环氧化和化学选择性醇氧化的组合，利用催化[(neocuproine)PdOAc]₂OTf₂，开发了一种新的合成科罗拉多马铃薯甲虫聚集信息素的方法。采用这种方法，从香叶醇出发，经过3个步骤，得到甲虫聚集信息素，产率为80%，ee为86%。