(2S)-1-[(2S,5S,7R,8R)-8-methyl-7-[(2R)-oxiran-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]hept-6-en-2-ol | 936016-68-1

• 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: (2S)-1-[(2S,5S,7R,8R)-8-methyl-7-[(2R)-oxiran-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]hept-6-en-2-ol
• CAS: 936016-68-1
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: UKSMUXMBYTXEQY-YRDXOGEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(2S,5S,7R,8R)-8-methyl-7-[(2R)-oxiran-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]hept-6-en-2-ol 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 5.5h， 生成 (-)-attenol A
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459
• 作为产物：
  描述：

  tert-butyl-[(2S)-1-[(2S,5R,7R,8R)-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-8-methyl-1,6-dioxaspiro[4.5]decan-2-yl]hept-6-en-2-yl]oxy-dimethylsilane 以67%的产率得到(2S)-1-[(2S,5S,7R,8R)-8-methyl-7-[(2R)-oxiran-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]hept-6-en-2-ol
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459

文献信息

• A Reductive Cyclization Approach to Attenol A
  作者：Thomas E. La Cruz、Scott D. Rychnovsky

  DOI：10.1021/jo0626459

  日期：2007.3.1

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.