5-[(2R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidine-2,4-dione | 1027202-34-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5-[(2R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidine-2,4-dione
• CAS: 1027202-34-1
• 化学式: C₂₅H₂₈N₂O₅Si
• 分子量: 464.593
• InChiKey: KSRAAWNCPUBRAA-IFMALSPDSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.17h， 生成 2',3'-dideoxy-3'-oxopseudouridine
  参考文献：
  名称：

  Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2',3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling

  摘要：

  5-Iodouracil and the ribofuranoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol underwent regio- and stereospecific coupling in the presence of catalytic palladium acetate and either triphenylphosphine or triphenylarsine ligands. The resulting C-glycosyl product was converted to 2'-deoxypseudouridine, 5-(2'-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione (63% overall yield). In a similar way, 2'-deoxyformycin B, 3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, and 2,3'-dideoxyformycin B, 3-(2',3'-dideoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, have been synthesized by reaction sequences in which the key step is a palladium-mediated regio- and stereospecific C-glycosyl bond forming reaction between this furanoid glycal and a bis(tetrahydropyranyl)-protected 3-iodopyrazolo[4,3-d]pyrimidine aglycon derivative.

  DOI：

  10.1021/jo00043a029
• 作为产物：
  描述：

  5-碘尿嘧啶 、 1,4-脱水-2-脱氧-3-O-[(叔丁基)二苯基硅]-D-赤式-戊-1-烯糖醇 在 palladium diacetate 三正丁胺 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 5-[(2R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2',3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling

  摘要：

  5-Iodouracil and the ribofuranoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol underwent regio- and stereospecific coupling in the presence of catalytic palladium acetate and either triphenylphosphine or triphenylarsine ligands. The resulting C-glycosyl product was converted to 2'-deoxypseudouridine, 5-(2'-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione (63% overall yield). In a similar way, 2'-deoxyformycin B, 3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, and 2,3'-dideoxyformycin B, 3-(2',3'-dideoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, have been synthesized by reaction sequences in which the key step is a palladium-mediated regio- and stereospecific C-glycosyl bond forming reaction between this furanoid glycal and a bis(tetrahydropyranyl)-protected 3-iodopyrazolo[4,3-d]pyrimidine aglycon derivative.

  DOI：

  10.1021/jo00043a029

文献信息

• Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2',3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling
  作者：Han Cheng Zhang、G. Doyle Daves

  DOI：10.1021/jo00043a029

  日期：1992.8

  5-Iodouracil and the ribofuranoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol underwent regio- and stereospecific coupling in the presence of catalytic palladium acetate and either triphenylphosphine or triphenylarsine ligands. The resulting C-glycosyl product was converted to 2'-deoxypseudouridine, 5-(2'-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione (63% overall yield). In a similar way, 2'-deoxyformycin B, 3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, and 2,3'-dideoxyformycin B, 3-(2',3'-dideoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, have been synthesized by reaction sequences in which the key step is a palladium-mediated regio- and stereospecific C-glycosyl bond forming reaction between this furanoid glycal and a bis(tetrahydropyranyl)-protected 3-iodopyrazolo[4,3-d]pyrimidine aglycon derivative.