(4S,5S)-3-tert-butyl-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-2-phenylethenyl]-1,3-oxazolidin-2-one | 1393478-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5S)-3-tert-butyl-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-2-phenylethenyl]-1,3-oxazolidin-2-one
• CAS: 1393478-31-3
• 化学式: C₂₂H₂₉NO₄
• 分子量: 371.477
• InChiKey: UBOAXRLGKMXBSZ-XHERKDLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-3-tert-butyl-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-2-phenylethenyl]-1,3-oxazolidin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以51%的产率得到(3aS,5aS,8aS,8bS)-6-tert-butyl-2,2-dimethyl-3a,5a,8a,8b-tetrahydro-[1,3]dioxolo[4,5-g][1,3]benzoxazol-7-one
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 咪唑 、 4-二甲氨基吡啶 、 vitamin B12 、 四丁基氟化铵 、 碘 、 氯化铵 、 三乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 39.75h， 生成 (4S,5S)-3-tert-butyl-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-2-phenylethenyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d