1-((2R,5S,6R)-5-(benzyloxymethoxy)-6-pentyltetrahydro-2H-pyran-2-yl)butan-2-one | 1618091-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,5S,6R)-5-(benzyloxymethoxy)-6-pentyltetrahydro-2H-pyran-2-yl)butan-2-one
• CAS: 1618091-82-9
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: IMXXUGGABJFZNP-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-((2R,5S,6R)-5-(benzyloxymethoxy)-6-pentyltetrahydro-2H-pyran-2-yl)butan-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以98%的产率得到decytospolide A
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以52.9 mg的产率得到1-((2R,5S,6R)-5-(benzyloxymethoxy)-6-pentyltetrahydro-2H-pyran-2-yl)butan-2-one
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p