(S)-3-(tert-butyldimethylsilyloxy)-6-oxodocosanoic acid | 913320-13-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-(tert-butyldimethylsilyloxy)-6-oxodocosanoic acid
• 英文别名: (3S)-3-[tert-butyl(dimethyl)silyl]oxy-6-oxodocosanoic acid
• CAS: 913320-13-5
• 化学式: C₂₈H₅₆O₄Si
• 分子量: 484.836
• InChiKey: HKWGYEHCGCCSJP-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  33
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)-6-oxodocosanoic acid 在 2-bromo-N-propylpyridinium triflate 、 4-吡咯烷基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以48%的产率得到(1R,2S,5S)-2-(tert-butyldimethylsilyloxy)-5-hexadecyl-6-oxabicyclo[3,2,0]heptan-7-one
  参考文献：
  名称：

  Bicyclic- and Tricyclic-β-lactones via Organonucleophile-Promoted Bis-Cyclizations of Keto Acids:  Enantioselective Synthesis of (+)-Dihydroplakevulin

  摘要：

  A highly diastereoselective, nucleophile-promoted bis-cyclization process, employing readily available and tractable keto acid substrates, is described. This methodology provides concise access to bicyclic- and tricyclic-beta-lactones bearing tertiary carbinol centers and quaternary carbons, greatly extending the scope of previous routes to bicyclic-beta-lactones from aldehyde acid substrates. The utility of the method was demonstrated by application to an enantioselective synthesis of (+)-dihydroplakevulin A. This and related processes may be revealing a subtle interplay between [2+2] cycloaddition and nucleophile-catalyzed aldol lactonization (NCAL) reaction manifolds.

  DOI：

  10.1021/ol061816t
• 作为产物：
  描述：

  在 lithium hydroxide 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (S)-3-(tert-butyldimethylsilyloxy)-6-oxodocosanoic acid
  参考文献：
  名称：

  Bicyclic- and Tricyclic-β-lactones via Organonucleophile-Promoted Bis-Cyclizations of Keto Acids:  Enantioselective Synthesis of (+)-Dihydroplakevulin

  摘要：

  A highly diastereoselective, nucleophile-promoted bis-cyclization process, employing readily available and tractable keto acid substrates, is described. This methodology provides concise access to bicyclic- and tricyclic-beta-lactones bearing tertiary carbinol centers and quaternary carbons, greatly extending the scope of previous routes to bicyclic-beta-lactones from aldehyde acid substrates. The utility of the method was demonstrated by application to an enantioselective synthesis of (+)-dihydroplakevulin A. This and related processes may be revealing a subtle interplay between [2+2] cycloaddition and nucleophile-catalyzed aldol lactonization (NCAL) reaction manifolds.

  DOI：

  10.1021/ol061816t

文献信息

• Bicyclic- and Tricyclic-β-lactones via Organonucleophile-Promoted Bis-Cyclizations of Keto Acids:  Enantioselective Synthesis of (+)-Dihydroplakevulin
  作者：Huda Henry-Riyad、Changsuk Lee、Vikram C. Purohit、Daniel Romo

  DOI：10.1021/ol061816t

  日期：2006.9

  A highly diastereoselective, nucleophile-promoted bis-cyclization process, employing readily available and tractable keto acid substrates, is described. This methodology provides concise access to bicyclic- and tricyclic-beta-lactones bearing tertiary carbinol centers and quaternary carbons, greatly extending the scope of previous routes to bicyclic-beta-lactones from aldehyde acid substrates. The utility of the method was demonstrated by application to an enantioselective synthesis of (+)-dihydroplakevulin A. This and related processes may be revealing a subtle interplay between [2+2] cycloaddition and nucleophile-catalyzed aldol lactonization (NCAL) reaction manifolds.