(5R)-5-benzyloxy-8-[(1S,3S)-3-methoxymethyl-1,2,2-trimethylcyclopentyl]-7-octyne-1,6-diol | 524705-99-5

• 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: (5R)-5-benzyloxy-8-[(1S,3S)-3-methoxymethyl-1,2,2-trimethylcyclopentyl]-7-octyne-1,6-diol
• CAS: 524705-99-5
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: DJBUPIFKQNCYCE-IQSHEIPESA-N

反应信息

• 作为反应物：
  描述：

  (5R)-5-benzyloxy-8-[(1S,3S)-3-methoxymethyl-1,2,2-trimethylcyclopentyl]-7-octyne-1,6-diol 在 dicobalt octacarbonyl 、 三氟化硼乙醚 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.75h， 生成 (2S,3R)-3-benzyloxy-2-[(1S,3S)-3-methoxymethyl-1,2,2-trimethyl-cyclopentylethynyl]-oxepane 、 (2R,3R)-3-benzyloxy-2-[(1S,3S)-3-methoxymethyl-1,2,2-trimethyl-cyclopentylethynyl]-oxepane
  参考文献：
  名称：

  Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations

  摘要：

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.

  DOI：

  10.1021/jo0340556
• 作为产物：
  描述：

  (R)-4-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-1-((1R,3S)-3-methoxymethyl-1,2,2-trimethyl-cyclopentyl)-oct-1-yn-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以165 mg的产率得到(5R)-5-benzyloxy-8-[(1S,3S)-3-methoxymethyl-1,2,2-trimethylcyclopentyl]-7-octyne-1,6-diol
  参考文献：
  名称：

  Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations

  摘要：

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.

  DOI：

  10.1021/jo0340556