(2R,3R,5S)-(+)-5-(1(S)-bromobut-3-enyl)-2-[2-(tert-butyldiphenylsilanyloxy)ethyl]tetrahydrofuran-3-ol | 927670-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5S)-(+)-5-(1(S)-bromobut-3-enyl)-2-[2-(tert-butyldiphenylsilanyloxy)ethyl]tetrahydrofuran-3-ol
• 英文别名: (2R,3R,5S)-5-[(1S)-1-bromobut-3-enyl]-2-[2-[tert-butyl(diphenyl)silyl]oxyethyl]oxolan-3-ol
• CAS: 927670-21-1
• 化学式: C₂₆H₃₅BrO₃Si
• 分子量: 503.552
• InChiKey: XAJMFKYWLCCRKF-LIONHTAISA-N

物化性质

• 沸点：
  540.5±48.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S)-(+)-5-(1(S)-bromobut-3-enyl)-2-[2-(tert-butyldiphenylsilanyloxy)ethyl]tetrahydrofuran-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以67%的产率得到(2R,3R,5S)-(-)-5-(1(S)-bromobut-3-enyl)-2-(2-hydroxyethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV

  摘要：

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

  DOI：

  10.1021/ol062818g
• 作为产物：
  描述：

  (3E)-3-己烯-1,6-二醇 在 正丁基锂 、 甲基磺酰胺 、 β-AD mix 、 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 41.0h， 生成 (2R,3R,5S)-(+)-5-(1(S)-bromobut-3-enyl)-2-[2-(tert-butyldiphenylsilanyloxy)ethyl]tetrahydrofuran-3-ol
  参考文献：
  名称：

  A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV

  摘要：

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

  DOI：

  10.1021/ol062818g

文献信息

• A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV
  作者：D. Christopher Braddock、Roshni Bhuva、David S. Millan、Yolanda Pérez-Fuertes、Craig A. Roberts、Richard N. Sheppard、Savade Solanki、Elaine S. E. Stokes、Andrew J. P. White

  DOI：10.1021/ol062818g

  日期：2007.2.1

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.