6-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methyl-5,6-dihydropyran-2-one | 1011482-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methyl-5,6-dihydropyran-2-one
• 英文别名: (5S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-one；(2R,3S)-2-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-3-methyl-2,3-dihydropyran-6-one
• CAS: 1011482-02-2
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: YOCRHOPCKHNTKV-SIKLNZKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methyl-5,6-dihydropyran-2-one 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (5S,6R)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-5-methyloxan-2-one
  参考文献：
  名称：

  Synthetic Efforts toward the Macrolactone Core of Leucascandrolide A

  摘要：

  [Graphics]A chemoselective synthesis of 1, the macrocyclic core of leucascandrolide A, has been achieved by utilizing highly enantioselective allylmetalations, an enantioselective Noyori reduction of a propargylic ketone, and olefin metatheses as the key steps.

  DOI：

  10.1021/jo701315h
• 作为产物：
  描述：

  (3R,4S)-1-((tert-butyldiphenylsilyl)oxy)-4-methylhex-5-en-3-yl acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以80 %的产率得到6-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

  摘要：

  AbstractIodide‐bound ruthenium‐JOSIPHOS complexes catalyze the redox‐neutral C−C coupling of primary alcohols with methylallene (1,2‐butadiene) or 1,3‐butadiene to form products of anti‐crotylation with good to excellent levels of diastereo‐ and enantioselectivity. Distinct from other methods, direct crotylation of primary alcohols in the presence of unprotected secondary alcohols is possible, enabling generation of spirastrellolide B (C9–C15) and leucascandrolide A (C9–C15) substructures in significantly fewer steps than previously possible.

  DOI：

  10.1002/anie.202212814