1-[(4S,5S)-4-(1-Bromo-vinyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 140209-52-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(4S,5S)-4-(1-Bromo-vinyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 140209-52-5；140209-53-6
• 化学式: C₂₈H₃₃BrN₂O₄Si
• 分子量: 569.571
• InChiKey: MXQORJFIYUQKAD-AEAWWFNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[(4S,5S)-4-(1-Bromo-vinyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 氢氧化钾 作用下， 以 丙醇 为溶剂， 以50%的产率得到1-((2R,4R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-ethynyltetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 3′-ethynylthymidine, 3′-vinylthymidine and 3′-bromovinylthymidine as potential antiviral agents

  摘要：

  The synthesis of three novel 3'-unsaturated carbon analogues of AZT and FLT is described. The key step in the synthesis is a Cu(I)- catalyzed addition of vinylmagnesium bromide to a 2,3-unsaturated lactone, followed by, in the case of compounds 2 and 3, elimination reactions of a dibromo-compound.

  DOI：

  10.1016/s0040-4039(00)92341-4
• 作为产物：
  描述：

  在 叔丁基二甲硅基三氟甲磺酸酯 4-二甲氨基吡啶 、 溴 、 sodium methylate 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 1-[(4S,5S)-4-(1-Bromo-vinyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 3′-ethynylthymidine, 3′-vinylthymidine and 3′-bromovinylthymidine as potential antiviral agents

  摘要：

  The synthesis of three novel 3'-unsaturated carbon analogues of AZT and FLT is described. The key step in the synthesis is a Cu(I)- catalyzed addition of vinylmagnesium bromide to a 2,3-unsaturated lactone, followed by, in the case of compounds 2 and 3, elimination reactions of a dibromo-compound.

  DOI：

  10.1016/s0040-4039(00)92341-4