1-<2-O-acetyl-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-arabinofuranosyl>uracil | 135824-37-2

• 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-O-acetyl-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-arabinofuranosyl>uracil
• 英文别名: [(2R,3R,4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)-4-phenylselanyloxolan-3-yl] acetate
• CAS: 135824-37-2
• 化学式: C₂₃H₃₂N₂O₆SeSi
• 分子量: 539.562
• InChiKey: VSTASSHBWTURFD-GFOJFJKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-<2-O-acetyl-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-arabinofuranosyl>uracil 在 间氯过氧苯甲酸 作用下， 以88%的产率得到Acetic acid (2R,3S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,3-dihydro-furan-3-yl ester
  参考文献：
  名称：

  Stereoselective synthesis of 4′-C-branched 2,′3′-didehydro-2′-dideoxy nucleosides based on SnCl4-promoted allylic rearrangement

  摘要：

  Based on SnCl4-promoted allylic rearrangement between a 3',4'-unsaturated uracil nucleoside and organosilicon reagents, stereoselective introduction of carbon functionalities to the 4'-position has been accomplished, disclosing a new entry for a series of 4'-C-branched nucleosides of biological interests.

  DOI：

  10.1016/s0040-4039(00)78874-5
• 作为产物：
  描述：

  5’-O-三苯甲基尿苷-2’,3’-来苏-环氧化物 在 吡啶 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 反应 2.67h， 生成 1-<2-O-acetyl-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-(phenylseleno)-β-D-arabinofuranosyl>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