1-<3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine | 135824-29-2

• 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-<3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine
• 英文别名: 1-[(2R,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-(phenylselanylmethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 135824-29-2
• 化学式: C₂₂H₃₂N₂O₄SeSi
• 分子量: 495.553
• InChiKey: XYGOVFAYIJYCBY-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine 在 三乙胺 、 间氯过氧苯甲酸 作用下， 生成 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-β-L-glycero-pent-4-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：

  1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到1-<3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>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