(4RS,5S)-5-cyclohexylmethyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide | 216855-31-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4RS,5S)-5-cyclohexylmethyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide
• 英文别名: ethyl (5S)-5-(cyclohexylmethyl)-4-hydroxy-2-oxido-4,5-dihydro-1,2-oxazol-2-ium-3-carboxylate
• CAS: 216855-31-1
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: WRNLFCSXMROGPS-NUHJPDEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  81.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 (4RS,5S)-5-cyclohexylmethyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以48%的产率得到(4R,5S)-4-(t-butyldiphenylsilyloxy)-5-cyclohexylmethyl-3-ethoxycarbonyl-2-isoxazoline 2-oxide
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i
• 作为产物：
  描述：

  (2R,3S,4S,5R)-1,6-dicyclohexyl-3,4-O-isopropylidene-2,5-di-O-(methanesulfonyl)-2,3,4,5-hexanetetraol 在 咪唑 、 盐酸 、 sodium periodate 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (4RS,5S)-5-cyclohexylmethyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i