(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-(phenylthio)ethyl]isoxazolidine-5-carboxylate | 1171098-26-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 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-(phenylthio)ethyl]isoxazolidine-5-carboxylate
• 英文别名: methyl (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-3-(2-phenylsulfanylethyl)-1,2-oxazolidine-5-carboxylate
• CAS: 1171098-26-2
• 化学式: C₂₆H₃₇NO₉S
• 分子量: 539.647
• InChiKey: LZOQTCCZWAGTGF-NJCBOKDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  11

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-(phenylthio)ethyl]isoxazolidine-5-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%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-(phenylsulfinyl)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：

  2-甲氧基-2-丙酸甲酯 、 3-phenylsulfanyl-propionaldehyde 、 2,3:5,6-di-O-isopropylidene-D-mannose oxime 以 甲苯 为溶剂， 反应 18.0h， 以32%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-(phenylthio)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

文献信息

• Synthesis of an enantiopure isoxazolidine monomer for β3-aspartic acid in chemoselective β-oligopeptide synthesis
  作者：Hiroshi Ishida、Nancy Carrillo、Jeffrey W. Bode

  DOI：10.1016/j.tetlet.2009.02.045

  日期：2009.7

  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.