(-)-(1S,3R,4S,7S,8R,11S)-4-(tert-butyldimethylsilyl)oxy-7,11-dimethyl-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane | 145332-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-(1S,3R,4S,7S,8R,11S)-4-(tert-butyldimethylsilyl)oxy-7,11-dimethyl-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane
• CAS: 145332-87-2
• 化学式: C₂₂H₃₉IO₄Si
• 分子量: 522.539
• InChiKey: RPRMBHHALFCUCE-BKTZOKNPSA-N

反应信息

• 作为反应物：
  描述：

  (-)-(1S,3R,4S,7S,8R,11S)-4-(tert-butyldimethylsilyl)oxy-7,11-dimethyl-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以83%的产率得到(-)-(1S,3R,4S,7S,8S,11S)-4-(tert-butyldimethylsilyl)oxy-7,11-dimethyl-8-hydroxymethyl-3-iodomethyl-2-oxatricyclo<6.4.0.0^3,7>dodecane
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3
• 作为产物：
  描述：

  methyl (1R,2S,4S)-1-<3-hydroxy-1-methyl-2-methylenecyclopentyl>-2-methoxy-4-methylcyclohexanecarboxylate 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 碘 、 碳酸氢钠 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.25h， 生成 (-)-(1S,3R,4S,7S,8R,11S)-4-(tert-butyldimethylsilyl)oxy-7,11-dimethyl-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3