3-(S)-O-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-γ-butyrolactol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3-(S)-O-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-γ-butyrolactol
• 英文别名: (2R,4S)-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-ol
• 化学式: C₁₀H₂₂O₃Si
• 分子量: 218.368
• InChiKey: LYMUSAXOONJCFL-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-3-t-butyldimethylsilyloxy-γ-butyrolactone 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 2-Furanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]tetrahydro-, (2S,4S)- 、 3-(S)-O-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-γ-butyrolactol
  参考文献：
  名称：

  A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond

  摘要：

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.

  DOI：

  10.1021/ja028617z

文献信息

• A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of <i>N</i>-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond
  作者：Jong Uk Rhee、Brian I. Bliss、T. V. RajanBabu

  DOI：10.1021/ja028617z

  日期：2003.2.1

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.