(2R,4R,1'R,2'R)-2-(2-azido-1-hydroxy-2-phenylethyl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester | 173099-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2R,4R,1'R,2'R)-2-(2-azido-1-hydroxy-2-phenylethyl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester
• CAS: 173099-22-4
• 化学式: C₂₀H₂₂N₄O₄
• 分子量: 382.419
• InChiKey: KWBDTLCFTXOBKZ-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  107.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,1'R,2'R)-2-(2-azido-1-hydroxy-2-phenylethyl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 72.25h， 生成 2-[(1R,2R)-2-azido-2-phenyl-1-phenylmethoxyethyl]-1,3-dithiolane
  参考文献：
  名称：

  Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of N-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis

  摘要：

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.

  DOI：

  10.1021/jo962277g
• 作为产物：
  描述：

  (2R,4R,2'E)-4-phenyl-2-(2-phenylvinyl)oxazolidine-3-carboxylic acid tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 氯化铵 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 (2R,4R,1'R,2'R)-2-(2-azido-1-hydroxy-2-phenylethyl)-4-phenyloxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of N-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis

  摘要：

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.

  DOI：

  10.1021/jo962277g