3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)pyrazolo<4,3-d>pyrimidin-7-one | 142189-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)pyrazolo<4,3-d>pyrimidin-7-one
• CAS: 142189-96-6
• 化学式: C₁₀H₁₀N₄O₄
• 分子量: 250.214
• InChiKey: OLNNMVRAKBNECX-NTSWFWBYSA-N

反应信息

• 作为产物：
  描述：

  (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 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.17h， 生成 3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)pyrazolo<4,3-d>pyrimidin-7-one
  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