(2S,3S)-1-hydroxy-2,3-di(t-butyldimethylsilyloxy)-pentane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S)-1-hydroxy-2,3-di(t-butyldimethylsilyloxy)-pentane
• 英文别名: (2S,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]pentan-1-ol
• 化学式: C₁₇H₄₀O₃Si₂
• 分子量: 348.674
• InChiKey: KZZDEKQVYOBHIC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• 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

• 作为反应物：
  描述：

  (2S,3S)-1-hydroxy-2,3-di(t-butyldimethylsilyloxy)-pentane 在 Lindlar's catalyst 吡啶 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 35.25h， 生成 (-)-(3R,4S)-(Z,Z)-6,9-cis-3,4-Epoxynonadecadiene
  参考文献：
  名称：

  Access to unsaturated chiral epoxides. Part. III1: Synthesis of a component of the sex pheromone of Boarmia selenaria

  摘要：

  A general method for the synthesis of chiral cis epoxides, which we have previously described, is used to synthetize the active enantiomer I of the sex pheromone of Boarmia selenaria.

  DOI：

  10.1016/0957-4166(95)00169-p
• 作为产物：
  描述：

  反-2-戊酸甲酯 在 咪唑 、 四氧化锇 、 甲基磺酰胺 、 水 、 二异丁基氢化铝 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 13.34h， 生成 (2S,3S)-1-hydroxy-2,3-di(t-butyldimethylsilyloxy)-pentane
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045

文献信息

• Total syntheses of four possible stereoisomers of resolvin E3
  作者：Daisuke Urabe、Hidenori Todoroki、Koji Masuda、Masayuki Inoue

  DOI：10.1016/j.tet.2012.02.045

  日期：2012.4

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.
• Access to unsaturated chiral epoxides. Part. III1: Synthesis of a component of the sex pheromone of Boarmia selenaria
  作者：J. Soulié、F. Péricaud、J.Y. Lallemand

  DOI：10.1016/0957-4166(95)00169-p

  日期：1995.6

  A general method for the synthesis of chiral cis epoxides, which we have previously described, is used to synthetize the active enantiomer I of the sex pheromone of Boarmia selenaria.