[(2S,3S)-2-triethylsilyloxolan-3-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate | 1138300-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [(2S,3S)-2-triethylsilyloxolan-3-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 1138300-78-3
• 化学式: C₂₀H₃₄O₅Si
• 分子量: 382.572
• InChiKey: FHKPOCBMBLPRRU-HZVDNRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-2-triethylsilyloxolan-3-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以77%的产率得到(2S,3S)-2-(triethylsilyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Asymmetric cycloetherification based on a chiral auxiliary for 4-acyloxy-1-butene substrates during oxidation with iodosylbenzene via a 1,3-dioxan-2-yl cation

  摘要：

  Reaction of but-3-enyl camphanate and its derivatives with iodosylbenzene yielded tetrahydrofuran-3-yl camphanate with high diastereomeric ratio via a 1,3-dioxan-2-yl cation intermediate. The reaction using (IS)-camphanate as a chiral auxiliary preferentially gave (S)-3-acyloxytetrahydrofuran and (2S,3S)-3-acyloxy-2-silyltetrahydrofuran. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.012
• 作为产物：
  描述：

  在 羟基甲苯磺酰碘苯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以49%的产率得到[(2S,3S)-2-triethylsilyloxolan-3-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Asymmetric cycloetherification based on a chiral auxiliary for 4-acyloxy-1-butene substrates during oxidation with iodosylbenzene via a 1,3-dioxan-2-yl cation

  摘要：

  Reaction of but-3-enyl camphanate and its derivatives with iodosylbenzene yielded tetrahydrofuran-3-yl camphanate with high diastereomeric ratio via a 1,3-dioxan-2-yl cation intermediate. The reaction using (IS)-camphanate as a chiral auxiliary preferentially gave (S)-3-acyloxytetrahydrofuran and (2S,3S)-3-acyloxy-2-silyltetrahydrofuran. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.012