[(3S,5R)-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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate | 951314-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(3S,5R)-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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate
• CAS: 951314-93-5
• 化学式: C₃₃H₄₀N₂O₁₀
• 分子量: 624.688
• InChiKey: KKLIHKNQZHEMOK-GLOPAVAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(3S,5R)-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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 153.0h， 生成 tert-butyl 2-[(3S,5R)-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-1,2-oxazolidin-2-yl]acetate
  参考文献：
  名称：

  3-(Aminomethyl)-2-(carboxymethyl)isoxazolidinyl nucleosides: building blocks for peptide nucleic acid analogues

  摘要：

  The synthesis of orthogonally protected 3-(aminomethyl)-2-(carboxymethyl)isoxazolidinyl thymine, a convenient monomer for the preparation of novel isoxazolidinyl peptide nucleic acid analogues, has been achieved through enantioselective 1,3-dipolar cyclo-addition between N-glycosyl nitrones and vinyl acetate. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.029
• 作为产物：
  描述：

  乙酸乙烯酯 、 (9H-芴-9-基)-2-氧代乙基氨基甲酸甲酯 、 2,3:5,6-di-O-isopropylidene-D-mannose oxime 反应 3.0h， 生成 [(3S,5R)-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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate 、 [(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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate 、 [(3R,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]-3-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,2-oxazolidin-5-yl] acetate
  参考文献：
  名称：

  3-(Aminomethyl)-2-(carboxymethyl)isoxazolidinyl nucleosides: building blocks for peptide nucleic acid analogues

  摘要：

  The synthesis of orthogonally protected 3-(aminomethyl)-2-(carboxymethyl)isoxazolidinyl thymine, a convenient monomer for the preparation of novel isoxazolidinyl peptide nucleic acid analogues, has been achieved through enantioselective 1,3-dipolar cyclo-addition between N-glycosyl nitrones and vinyl acetate. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.029