(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol | 1109222-01-6

• 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,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol
• 英文别名: (2R,3S)-1-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethyloct-6-ene-2,3-diol
• CAS: 1109222-01-6
• 化学式: C₂₆H₃₈O₃Si
• 分子量: 426.671
• InChiKey: APGKNZOLQZYBNA-RSXGOPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以95%的产率得到(S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  从其降解产物合成科罗拉多马铃薯甲虫的聚集信息素

  摘要：

  将科罗拉多马铃薯甲虫聚集信息素（S）-1,3-二羟基-3,7-二甲基-6-辛烯-2-酮与该甲虫的触角或腿部提取物一起孵育，得到6-甲基-5-庚烯-二合一为主要产品。该酮用作信息素的立体选择性合成中的底物。将其以良好的立体选择性连接到乙醇酸的丁二缩醛上，并通过在硅胶上纯化该反应的产物来进一步富集所需的异构体。

  DOI：

  10.1016/j.bmcl.2015.06.083
• 作为产物：
  描述：

  (3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-[(1S)-1,5-dimethyl-1-hydroxyhex-4-enyl]-1,4-dioxan-2-one 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol
  参考文献：
  名称：

  从其降解产物合成科罗拉多马铃薯甲虫的聚集信息素

  摘要：

  将科罗拉多马铃薯甲虫聚集信息素（S）-1,3-二羟基-3,7-二甲基-6-辛烯-2-酮与该甲虫的触角或腿部提取物一起孵育，得到6-甲基-5-庚烯-二合一为主要产品。该酮用作信息素的立体选择性合成中的底物。将其以良好的立体选择性连接到乙醇酸的丁二缩醛上，并通过在硅胶上纯化该反应的产物来进一步富集所需的异构体。

  DOI：

  10.1016/j.bmcl.2015.06.083

文献信息

• 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%。
• Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer
  作者：Shuo-Ning Li、Ling-Lan Fang、Jiang-Chun Zhong、Jun-Jian Shen、Hao Xu、Yan-Qing Yang、Shi-Cong Hou、Qing-hua Bian

  DOI：10.1016/j.tetasy.2013.12.018

  日期：2014.4

  An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethy1-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate. (C) 2014 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol: a Colorado potato beetle pheromone
  作者：Bathini Nagendra Babu、Kamlesh R. Chauhan

  DOI：10.1016/j.tetlet.2008.10.092

  日期：2009.1

  The recent identification of a male-produced aggregation pheromone [(S)-3,7-dimethyl-2-oxo-6-octene1,3-diol, (S)-CPB] offers a new tool for Colorado potato beetle (CPB) management. We developed a novel synthetic approach to produce CPB pheromone in seven steps and 46.54% overall yield. Grignard reaction, oxidation, and stereoselective methylation using organometallic reagent are the key steps in the commercially viable total synthesis, generating CPB pheromone in 98.6% enantiomeric purity and gram quantity. Published by Elsevier Ltd.
• Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product
  作者：Weronika Wacławczyk-Biedroń、Bożena Frąckowiak-Wojtasek、Daniel Strub、Magdalena Rzechak、Hubert Wojtasek

  DOI：10.1016/j.bmcl.2015.06.083

  日期：2015.9

  Incubation of the Colorado potato beetle aggregation pheromone, (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, with antennal or leg extracts from this beetle gave 6-methyl-5-hepten-2-one as the major product. This ketone was used as a substrate in a stereoselective synthesis of the pheromone. It was attached to the butanediacetal of glycolic acid with good stereoselectivity and the desired isomer was

  将科罗拉多马铃薯甲虫聚集信息素（S）-1,3-二羟基-3,7-二甲基-6-辛烯-2-酮与该甲虫的触角或腿部提取物一起孵育，得到6-甲基-5-庚烯-二合一为主要产品。该酮用作信息素的立体选择性合成中的底物。将其以良好的立体选择性连接到乙醇酸的丁二缩醛上，并通过在硅胶上纯化该反应的产物来进一步富集所需的异构体。