2',3'-dideoxyformycin B | 142189-82-0

• 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: 2',3'-dideoxyformycin B
• 英文别名: 3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one
• CAS: 142189-82-0
• 化学式: C₁₀H₁₂N₄O₃
• 分子量: 236.23
• InChiKey: URILDWKLQKGROF-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(2',3'-dideoxy-β-D-ribofuranosyl)-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以88%的产率得到2',3'-dideoxyformycin B
  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

• Efficient synthesis of 2′,3′-dideoxynucleosides and 2′,3′-dideoxy C-nucleosides from D-glucosamine
  作者：Michael E. Jung、Ivan D. Trifunovich

  DOI：10.1016/s0040-4039(00)79561-x

  日期：1992.5

  D-Glucosamine 1 can be easily converted into 2,5-anhydro-6-O-benzoyl-3,4-dideoxygluconic acid 6 which can be taken on to both 2′,3′-dideoxynucleosides such as dideoxyuridine (ddU) 4 and 2′,3′-dideoxy C-nucleosides such as dideoxyformycin B 5 and dideoxyshowdomycin 20.

  D-葡糖胺1可以轻松转化为2,5-脱水-6- O-苯甲酰基-3,4-二脱氧葡萄糖酸6，可以同时用于2'，3'-二脱氧核苷，例如双脱氧尿苷（ddU）4和2'，3'-二脱氧C-核苷，例如双脱氧福霉素B 5和双脱氧showdomycin 20。