(1S,2R,5R,7S)-2-hydroxy-exo-brevicomin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,2R,5R,7S)-2-hydroxy-exo-brevicomin
• 英文别名: (-)-2-hydroxy-exo-brevicomin；(1S,2R,5R,7S)-7-Ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-ol
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: PFDZIEBTGBMYIS-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 palladium on activated charcoal sodium periodate 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (1S,2R,5R,7S)-2-hydroxy-exo-brevicomin
  参考文献：
  名称：

  为（1的合成方法Chiron公司小号，2 - [R，5 - [R 7小号）-2-羟基-外型-brevicomin

  摘要：

  （1级小号，2 - [R，5 - [R 7小号）-2-羟基-外型-brevicomin ENT - 1从1,2-合成; 5,6-二- ö异亚丙基d葡萄糖在七个步骤。我们合成过程中的关键反应是在D-葡萄糖衍生物6的1,2-丙酮化物的酸介导的乙缩醛交换下形成双环缩酮7。

  DOI：

  10.1016/j.tetasy.2006.02.020

文献信息

• Pheromone Synthesis, CLXXXIII. Synthesis of (1R,2R,5S,7R)- and (1R,2S,5S,7R)-2-hydroxy-exo-Brevicomin, the Components of the Male-Produced Volatiles of the Mountain Pine Beetle,dendroctonus ponderosae
  作者：Hirosato Takikawa、Ken-Ichiro Shimbo、Kenji Mori

  DOI：10.1002/jlac.199719970506

  日期：1997.5

  Both (2R)- and (2S)-hydroxy derivatives of (+)-exo-brevicomin 5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-ol; 1 and 2} were synthesized by employing Sharpless asymmetric dihydroxylation as the key reaction.

  （+）-exo-brevicomin 5-甲基-6,8-二氧杂双环[3.2.1] octan-2-ol;的（2 R）-和（2 S）-羟基衍生物。1和2 }是通过采用Sharpless不对称二羟基化反应为关键反应而合成的。
• Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-<i>exo</i>-brevicomin
  作者：Dimitris Noutsias、Antonia Kouridaki、Georgios Vassilikogiannakis

  DOI：10.1021/ol200027f

  日期：2011.3.4

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.
• Enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2006.02.023

  日期：2006.3

  An enantiospecific synthesis of (-)-2-hydroxy-exo-brevicomin was achieved from, (L)-(+)-tartaric acid in high yield. The key step involves a very highly diastereoselective reduction of a keto Weinreb amide. (c) 2006 Elsevier Ltd. All rights reserved.