7-(2-Deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,7-dihydro-2-methyl-5-phenyl-3-(4-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine | 173976-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-(2-Deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,7-dihydro-2-methyl-5-phenyl-3-(4-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine
• 英文别名: 7-(2-Deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,7-dihydro-2-methyl-5-phenyl-3-(4-fluorophenyl)-4H-pyrrolo[2,3-d]pyrimidin-4-imine；[(2R,3S,5R)-5-[3-(4-fluorophenyl)-4-imino-2-methyl-5-phenylpyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 173976-84-6
• 化学式: C₄₀H₃₅FN₄O₅
• 分子量: 670.74
• InChiKey: SKOJWKINANFSJW-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(2-Deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,7-dihydro-2-methyl-5-phenyl-3-(4-fluorophenyl)-4H-pyrrolo<2,3-d>pyrimidin-4-imine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以68%的产率得到7-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-3-(4-fluorophenyl)-2-methyl-5-phenyl-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
• 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 、 3-(4-Fluorophenyl)-3,7-dihydro-2-methyl-5-phenyl-4H-pyrrolo<2,3-d>pyrimidin-4-imine 在 sodium hydride 作用下， 以 乙腈 为溶剂， 以80%的产率得到7-(2-Deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,7-dihydro-2-methyl-5-phenyl-3-(4-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.