1-<2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-xylofuranosyl>uracil | 135824-33-8

• 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-<2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-xylofuranosyl>uracil
• 英文别名: 1-[(2R,3S,4S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylselanyloxolan-2-yl]pyrimidine-2,4-dione
• CAS: 135824-33-8
• 化学式: C₂₇H₄₄N₂O₅SeSi₂
• 分子量: 611.788
• InChiKey: MXKRPWSMPGCURR-CAUSLRQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-xylofuranosyl>uracil 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 以71%的产率得到1-[(2R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  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：

  二苯基二硒醚 在 咪唑 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 1-<2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-xylofuranosyl>uracil
  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