(4S,5S)-5-butyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide

• 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: (4S,5S)-5-butyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide
• 英文别名: ethyl (4S,5S)-5-butyl-4-hydroxy-2-oxido-4,5-dihydro-1,2-oxazol-2-ium-3-carboxylate
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: DMIQGBQGSVJZBP-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二甲基乙烯基氯硅烷 、 (4S,5S)-5-butyl-3-ethoxycarbonyl-4-hydroxy-2-isoxazoline 2-oxide 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到(2aR,6S,6aS,6bR)-6-Butyl-2,2-dimethyl-tetrahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]pentalene-6b-carboxylic acid ethyl ester
  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：

  (4S,5S)-5-butyl-4-(t-butyldiphenylsilyloxy)-3-ethoxycarbonyl-2-isoxazoline 2-oxide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (4S,5S)-5-butyl-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

文献信息

• Stereocontrolled synthesis of 3-(ethoxycarbonyl)-4-hydroxy-2-isoxazoline-2-oxides. A new approach to the synthesis of 4-hydroxylated 2-isoxazolines
  作者：Goffredo Rosini、Emanuela Marotta、Paolo Righi、Jean Paul Seerden

  DOI：10.1021/jo00022a005

  日期：1991.10

  Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereoisomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of trans and cis 4-hydroxylated 2-isoxazolines in a predictable way.
• <scp>d</scp>-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems
  作者：Emanuela Marotta、Marco Baravelli、Luigi Maini、Paolo Righi、Goffredo Rosini

  DOI：10.1021/jo980941i

  日期：1998.11.1

  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.