5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine | 135824-27-0

• 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: 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylselanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 135824-27-0
• 化学式: C₂₂H₃₂N₂O₄SeSi
• 分子量: 495.553
• InChiKey: ZAYAJIBKIIGEJX-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
  参考文献：
  名称：

  Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides

  摘要：

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.

  DOI：

  10.1021/jo00018a038
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine
  参考文献：
  名称：

  Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides

  摘要：

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.

  DOI：

  10.1021/jo00018a038