[(1R,2S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate | 853234-43-2

• 分子结构分类: 有机化合物
• 英文名称: [(1R,2S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate
• CAS: 853234-43-2
• 化学式: C₂₁H₄₀O₅Si₂
• 分子量: 428.717
• InChiKey: ZJFLFNFJPFRVER-OKYOBFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以68%的产率得到(1R,2S,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-ol
  参考文献：
  名称：

  Enantioselective total synthesis of polyoxygenated cyclohexanoids: (+)-streptol, ent-RKTS-33 and putative ‘(+)-parasitenone’. Identity of parasitenone with (+)-epoxydon

  摘要：

  Short, simple and enantioselective syntheses of the natural product (+)-streptol, the non-peptide apoptosis inhibitor ent-RKTS-33 and the putative structure of 'parasitenone' have been accomplished from the readily available chiral building block. 'Parasitenone' has been shown to be identical with the known natural product epoxydon. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.087
• 作为产物：
  描述：

  [(1R,2S,3S,4R,6R,8R,9S)-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxo-5-oxatetracyclo[7.2.1.02,8.04,6]dodec-10-en-3-yl] acetate 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 二苯醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 [(1R,2S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate
  参考文献：
  名称：

  Enantioselective total synthesis of polyoxygenated cyclohexanoids: (+)-streptol, ent-RKTS-33 and putative ‘(+)-parasitenone’. Identity of parasitenone with (+)-epoxydon

  摘要：

  Short, simple and enantioselective syntheses of the natural product (+)-streptol, the non-peptide apoptosis inhibitor ent-RKTS-33 and the putative structure of 'parasitenone' have been accomplished from the readily available chiral building block. 'Parasitenone' has been shown to be identical with the known natural product epoxydon. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.087