(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanol | 219958-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanol
• CAS: 219958-07-3
• 化学式: C₁₆H₃₂O₅Si
• 分子量: 332.513
• InChiKey: CMLBWARHMQGTOW-QNSTZXKLSA-N

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanone
  参考文献：
  名称：

  Synthesis of (−)-Isonitrin B

  摘要：

  The first enantioselective synthesis of (-)-isonitrin B (2), the parent of a small family of isonitrile antibiotics having compact but highly functionalized (and highly reactive) cyclopentane rings, is described. They key in this synthesis is the cyclization of 5b to 4b, by way of the intermediate alkylidene carbene.

  DOI：

  10.1021/ja981700v
• 作为产物：
  描述：

  (S)-2-Benzyloxy-1-[(2R,3R)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 生成 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R)-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-ethanol
  参考文献：
  名称：

  Synthesis of (−)-Isonitrin B

  摘要：

  The first enantioselective synthesis of (-)-isonitrin B (2), the parent of a small family of isonitrile antibiotics having compact but highly functionalized (and highly reactive) cyclopentane rings, is described. They key in this synthesis is the cyclization of 5b to 4b, by way of the intermediate alkylidene carbene.

  DOI：

  10.1021/ja981700v