3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine | 142189-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine
• 英文别名: Tert-butyl-[1-[tert-butyl(diphenyl)silyl]-3-iodopyrazolo[4,3-d]pyrimidin-7-yl]oxy-diphenylsilane
• CAS: 142189-89-7
• 化学式: C₃₇H₃₉IN₄OSi₂
• 分子量: 738.818
• InChiKey: WGVDMJIRUNKURQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三正丁胺 、 三苯胂 、 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol 、 对甲苯磺酸 作用下， 生成 1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 、 (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 、 1,1'-bis(tetrahydropyran-2-yl)-7,7'-bis<(tetrahydropyran-2-yl)oxy>3,3'-bispyrimidine>
  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：

  7-羟基吡唑并[4,3-d]嘧啶 在 N-碘代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine
  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