1-[(5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2-oxazolidin-5-yl]-4-aminopyrimidin-2-one | 557794-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2-oxazolidin-5-yl]-4-aminopyrimidin-2-one
• CAS: 557794-50-0
• 化学式: C₃₁H₄₀N₄O₆Si
• 分子量: 592.767
• InChiKey: BBHJXIMKBIJGFR-BYUBTRPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2-oxazolidin-5-yl]-4-aminopyrimidin-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到4-Amino-1-(S)-isoxazolidin-5-yl-1H-pyrimidin-2-one
  参考文献：
  名称：

  Enantioselective Syntheses and Cytotoxicity of N,O-Nucleosides

  摘要：

  Enantiomers of 4'-aza-2',3'-dideoxynucleosides have been prepared by two different synthetic approaches, on the basis of 1,3-dipolar cycloaddition of a chiral nitrone. Cytotoxicity and apoptotic activity have been investigated. (5'S)-5-Fluoro-1-isoxazolidin-5-yl-1H-pyrimidine-2,4-dione [(-)-AdFU], while showing low level of cytotoxicity, is a good inductor of apoptosis on lymphoid and monocytoid cells, acting as a strong potentiator of Fas-induced cell death.

  DOI：

  10.1021/jm0308186
• 作为产物：
  描述：

  胞嘧啶 、 在 牛血清白蛋白 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以44%的产率得到1-[(5R)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2-oxazolidin-5-yl]-4-aminopyrimidin-2-one
  参考文献：
  名称：

  Enantioselective Syntheses and Cytotoxicity of N,O-Nucleosides

  摘要：

  Enantiomers of 4'-aza-2',3'-dideoxynucleosides have been prepared by two different synthetic approaches, on the basis of 1,3-dipolar cycloaddition of a chiral nitrone. Cytotoxicity and apoptotic activity have been investigated. (5'S)-5-Fluoro-1-isoxazolidin-5-yl-1H-pyrimidine-2,4-dione [(-)-AdFU], while showing low level of cytotoxicity, is a good inductor of apoptosis on lymphoid and monocytoid cells, acting as a strong potentiator of Fas-induced cell death.

  DOI：

  10.1021/jm0308186

文献信息

• Enantioselective Syntheses and Cytotoxicity of <i>N</i>,<i>O</i>-Nucleosides
  作者：Ugo Chiacchio、Antonino Corsaro、Daniela Iannazzo、Anna Piperno、Venerando Pistarà、Antonio Rescifina、Roberto Romeo、Vincenza Valveri、Antonio Mastino、Giovanni Romeo

  DOI：10.1021/jm0308186

  日期：2003.8.1

  Enantiomers of 4'-aza-2',3'-dideoxynucleosides have been prepared by two different synthetic approaches, on the basis of 1,3-dipolar cycloaddition of a chiral nitrone. Cytotoxicity and apoptotic activity have been investigated. (5'S)-5-Fluoro-1-isoxazolidin-5-yl-1H-pyrimidine-2,4-dione [(-)-AdFU], while showing low level of cytotoxicity, is a good inductor of apoptosis on lymphoid and monocytoid cells, acting as a strong potentiator of Fas-induced cell death.