4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilylmethanol | 1258381-54-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilylmethanol
• 英文别名: [[4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-5-methylsulfanylfuran-2-yl]-dimethylsilyl]methanol；[[4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methylsulfanylfuran-2-yl]-dimethylsilyl]methanol
• CAS: 1258381-54-2
• 化学式: C₁₅H₃₀O₃SSi₂
• 分子量: 346.638
• InChiKey: ADCYOFQRKCBPED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilylmethanol 、 5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以72%的产率得到((5,8-bisbenzyloxy-2-chloro-4-3S,4R,5R,6R-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-2H-pyran-2-ylnaphthalen-1-yloxy)methyl)4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilane
  参考文献：
  名称：

  Approach Toward the Total Synthesis of 5-Hydroxyaloin A

  摘要：

  The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.

  DOI：

  10.1021/ol102318k
• 作为产物：
  描述：

  3-呋喃甲醇 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 4-tert-butyldimethylsilyloxymethyl-5-(methylthio)furan-2-yldimethylsilylmethanol
  参考文献：
  名称：

  Approach Toward the Total Synthesis of 5-Hydroxyaloin A

  摘要：

  The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.

  DOI：

  10.1021/ol102318k

文献信息

• Approach Toward the Total Synthesis of 5-Hydroxyaloin A
  作者：Kristen J. Procko、Hui Li、Stephen F. Martin

  DOI：10.1021/ol102318k

  日期：2010.12.17

  The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.