(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 | 1171098-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 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-carboxyethyl]isoxazolidine-5-carboxylate
• 英文别名: 2-[(3S,5S)-2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-methoxy-5-methoxycarbonyl-1,2-oxazolidin-3-yl]acetic acid
• CAS: 1171098-36-4
• 化学式: C₂₀H₃₁NO₁₁
• 分子量: 461.466
• InChiKey: BXAYERTZSKMPEO-VIJNRQOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-叔丁基-1,3-二异丙基异脲 、 (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 以 甲苯 为溶剂， 反应 10.0h， 以58%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-(tert-butoxycarbonyl)ethyl]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-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