(2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-oxoethyl]isoxazolidine-5-carboxylate | 1171098-34-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-oxoethyl]isoxazolidine-5-carboxylate
• CAS: 1171098-34-2
• 化学式: C₂₀H₃₁NO₁₀
• 分子量: 445.467
• InChiKey: GEBGDGZRWNMIBK-UTTQJGMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  111.22
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-oxoethyl]isoxazolidine-5-carboxylate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.33h， 以96%的产率得到(2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-carboxyethyl]isoxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of an enantiopure isoxazolidine monomer for β3-aspartic acid in chemoselective β-oligopeptide synthesis

  摘要：

  The synthesis of an enantiopure isoxazolidine monomer for the incorporation of beta(3)-aspartic acid residues into beta(3)-oligopeptides via chemoselective alpha-ketoacid-hydroxylamine amide formation is disclosed. This route involves nitrone cycloaddition of 3-thiophenylpropanal and Circumvents limitations of other potential starting Materials. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.045
• 作为产物：
  描述：

  (2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-(phenylsulfinyl)ethyl]isoxazolidine-5-carboxylate 在 2,6-二甲基吡啶 、 三氟乙酸酐 、 碳酸氢钠 、 mercury dichloride 作用下， 以 乙腈 、 水 为溶剂， 反应 2.33h， 以95%的产率得到(2S,5S)-methyl 2-{(3aS,4S,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-5-methoxy-3-[2-oxoethyl]isoxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of an enantiopure isoxazolidine monomer for β3-aspartic acid in chemoselective β-oligopeptide synthesis

  摘要：

  The synthesis of an enantiopure isoxazolidine monomer for the incorporation of beta(3)-aspartic acid residues into beta(3)-oligopeptides via chemoselective alpha-ketoacid-hydroxylamine amide formation is disclosed. This route involves nitrone cycloaddition of 3-thiophenylpropanal and Circumvents limitations of other potential starting Materials. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.045