(Z,1R)-1-[(2R,3R)-3-methyl-3,6-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-en-1-ol | 936016-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (Z,1R)-1-[(2R,3R)-3-methyl-3,6-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-en-1-ol
• CAS: 936016-81-8
• 化学式: C₂₁H₄₀O₃Si
• 分子量: 368.632
• InChiKey: GWCCJYFJCWLXQF-VJMALODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z,1R)-1-[(2R,3R)-3-methyl-3,6-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-en-1-ol 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到[(Z,1R)-1-[(2R,3R)-3-methyl-3,6-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-enoxy]-tri(propan-2-yl)silane
  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：

  but-3-ynyloxy-triisopropyl-silane 在 indium(III) chloride 、 正丁基锂 、 三乙基硼 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 6.0h， 生成 (Z,1R)-1-[(2R,3R)-3-methyl-3,6-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-en-1-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.