(1S,2S,4R,6R)-2-(tert-butyldimethylsilyloxy)-4-acetyl-1-methyl-7-oxabicyclo[4.1.0]heptane | 205681-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,2S,4R,6R)-2-(tert-butyldimethylsilyloxy)-4-acetyl-1-methyl-7-oxabicyclo[4.1.0]heptane
• 英文别名: 1-[(1R,3R,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl]ethanone
• CAS: 205681-01-2
• 化学式: C₁₅H₂₈O₃Si
• 分子量: 284.471
• InChiKey: TWDFTXZIDOCAKG-GUIRCDHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,6R)-2-(tert-butyldimethylsilyloxy)-4-acetyl-1-methyl-7-oxabicyclo[4.1.0]heptane 在 2,2,6,6-四甲基哌啶 、 咪唑 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 四丁基氟化铵 、 氯化二乙基铝 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 phosphate buffer 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 65.5h， 生成 (2R,5R,7R,9S,10S)-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxin-7-ol
  参考文献：
  名称：

  Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides

  摘要：

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.

  DOI：

  10.1021/jo972285c
• 作为产物：
  描述：

  tert-butyl-[(1S,2S,4R,6R)-4-iso-propenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yloxy]dimethylsilane 在 四氧化锇 potassium metaperiodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以83%的产率得到(1S,2S,4R,6R)-2-(tert-butyldimethylsilyloxy)-4-acetyl-1-methyl-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides

  摘要：

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.

  DOI：

  10.1021/jo972285c

文献信息

• Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides
  作者：Jing Wang、Roger Busson、Norbert Blaton、Jef Rozenski、Piet Herdewijn

  DOI：10.1021/jo972285c

  日期：1998.5.1

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.