(1R,2S,5S)-2-(tert-butyldimethylsilyloxy)-5-hexadecyl-6-oxabicyclo[3,2,0]heptan-7-one | 913320-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2S,5S)-2-(tert-butyldimethylsilyloxy)-5-hexadecyl-6-oxabicyclo[3,2,0]heptan-7-one
• 英文别名: (1R,2S,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-hexadecyl-6-oxabicyclo[3.2.0]heptan-7-one
• CAS: 913320-14-6
• 化学式: C₂₈H₅₄O₃Si
• 分子量: 466.82
• InChiKey: TYQIIFLEHHUNGF-VBOOUTDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.95
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S)-2-(tert-butyldimethylsilyloxy)-5-hexadecyl-6-oxabicyclo[3,2,0]heptan-7-one 在 吡啶 、 氢氟酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (+)-dihydroplakevulin A
  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：

  (S)-methyl 3-(tert-butyldimethylsilyloxy)-6-oxodocosanoate 在 2-bromo-N-propylpyridinium triflate 、 lithium hydroxide 、 4-吡咯烷基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (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