7-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2,5-dimethyl-3-(2-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine | 173976-87-9

• 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: 7-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2,5-dimethyl-3-(2-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine
• 英文别名: (2R,3S,5R)-5-[3-(2-fluorophenyl)-4-imino-2,5-dimethylpyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 173976-87-9
• 化学式: C₁₉H₂₁FN₄O₃
• 分子量: 372.399
• InChiKey: JKCGEQGTPKZULB-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2,5-dimethyl-3-(2-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine 以 水 为溶剂， 以41%的产率得到7-(2-Deoxy-β-D-erythro-pentofuranosyl)-2,5-dimethyl-4-(2-fluorophenylamino)-7H-pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  Synthese und Reaktionen von 2-Deoxy-?-D-ribofuranosylderivaten von 3-Aryl-4H-pyrrolo[2,3-d]pyrimidin-4-iminen

  摘要：

  3-Aryl-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-imines (4) as well as 4-arylamino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-2-methyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidines (7) have been synthesized by glycosylation of the sodium salt of the corresponding nucleobases with 2-deoxy-3,5-di-O-p-toluyl-beta-D-erythro-pentofuranosyl chloride (2) followed by subsequent deprotection with sodium methoxide in methanol. The deprotected nucleoside 4 undergoes a Dimroth rearrangement on reflux for 24h in water to furnish the 4-arylamino nucleoside 7.

  DOI：

  10.1007/bf00824307
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 7-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2,5-dimethyl-3-(2-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine
  参考文献：
  名称：

  Synthese und Reaktionen von 2-Deoxy-?-D-ribofuranosylderivaten von 3-Aryl-4H-pyrrolo[2,3-d]pyrimidin-4-iminen

  摘要：

  3-Aryl-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-imines (4) as well as 4-arylamino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-2-methyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidines (7) have been synthesized by glycosylation of the sodium salt of the corresponding nucleobases with 2-deoxy-3,5-di-O-p-toluyl-beta-D-erythro-pentofuranosyl chloride (2) followed by subsequent deprotection with sodium methoxide in methanol. The deprotected nucleoside 4 undergoes a Dimroth rearrangement on reflux for 24h in water to furnish the 4-arylamino nucleoside 7.

  DOI：

  10.1007/bf00824307

文献信息

• Synthese und Reaktionen von 2-Deoxy-?-D-ribofuranosylderivaten von 3-Aryl-4H-pyrrolo[2,3-d]pyrimidin-4-iminen
  作者：M. A. Zahran、E. B. Pedersen、C. Nielsen

  DOI：10.1007/bf00824307

  日期：1995.11

  3-Aryl-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-imines (4) as well as 4-arylamino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-2-methyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidines (7) have been synthesized by glycosylation of the sodium salt of the corresponding nucleobases with 2-deoxy-3,5-di-O-p-toluyl-beta-D-erythro-pentofuranosyl chloride (2) followed by subsequent deprotection with sodium methoxide in methanol. The deprotected nucleoside 4 undergoes a Dimroth rearrangement on reflux for 24h in water to furnish the 4-arylamino nucleoside 7.