(1S,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclooctane-1,3-diol | 847776-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclooctane-1,3-diol
• CAS: 847776-44-7
• 化学式: C₁₄H₃₀O₃Si
• 分子量: 274.476
• InChiKey: DJLBIEKFOQTBEZ-CLLJXQQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclooctane-1,3-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到cyclooctane-1,2,3-triol
  参考文献：
  名称：

  From Common Carbohydrates to Enantiopure Cyclooctane Polyols and Glycomimetics via Deoxygenative Zirconocene Ring Contraction

  摘要：

  D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol. Subsequently defined are convenient synthetic routes to several cyclooctane-1,2,3-triols, 1,2,3,4,5-pentaols, and structurally related glycomimetics.

  DOI：

  10.1021/jo051989g
• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-4-vinylcyclobutanol 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 苯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 10.0h， 生成 (1S,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclooctane-1,3-diol
  参考文献：
  名称：

  From Common Carbohydrates to Enantiopure Cyclooctane Polyols and Glycomimetics via Deoxygenative Zirconocene Ring Contraction

  摘要：

  D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol. Subsequently defined are convenient synthetic routes to several cyclooctane-1,2,3-triols, 1,2,3,4,5-pentaols, and structurally related glycomimetics.

  DOI：

  10.1021/jo051989g

文献信息

• Enantioselective Route from Carbohydrates to Cyclooctane Polyols
  作者：Leo A. Paquette、Yunlong Zhang

  DOI：10.1021/ol0474296

  日期：2005.2.1

  A synthetic route to select cyclooctane-1,2,3-triols and 1,2,3,4,5-pentaols has been defined. The starting materials are D-glucose or D-arabinose, and the key steps consist of a zirconocene-promoted ring contraction, a [3,3] sigmatropic rearrangement, and more extended functionalization of the resulting cyclooctadienone.