4-amino-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one | 698376-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one
• 英文别名: [(2R,3S,5R)-5-(4-amino-2-oxo-3H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 698376-58-8
• 化学式: C₂₇H₂₆N₄O₆
• 分子量: 502.527
• InChiKey: LKTDFZIKMOUZRK-BHDDXSALSA-N

物化性质

• 熔点：
  70-75 °C(Solvent: Dichloromethane ; Hexane)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one
  参考文献：
  名称：

  Artificial Genetic Systems:  Exploiting the “Aromaticity” Formalism To Improve the Tautomeric Ratio for Isoguanosine Derivatives

  摘要：

  The tautomerism of 2'-deoxy-7-deaza-isoguanosine (2) was studied and compared to that of 2'-deoxyisoguanosine (1). The fixed N-1-methyl (8) and O-methyl (4) derivatives were synthesized to represent the pure extremes of each tautomer. The replacement of the imidazole ring in 1 with a pyrrole ring in 2 makes the keto form in the latter more favored by 2 orders of magnitude (K-TAUT for 2 approximate to 10(3), as opposed to K-TAUT for 1 approximate to 10).

  DOI：

  10.1021/jo0497959
• 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 hydride 、 苯硫酚 作用下， 以 乙二醇 、 乙腈 为溶剂， 生成 4-amino-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  Artificial Genetic Systems:  Exploiting the “Aromaticity” Formalism To Improve the Tautomeric Ratio for Isoguanosine Derivatives

  摘要：

  The tautomerism of 2'-deoxy-7-deaza-isoguanosine (2) was studied and compared to that of 2'-deoxyisoguanosine (1). The fixed N-1-methyl (8) and O-methyl (4) derivatives were synthesized to represent the pure extremes of each tautomer. The replacement of the imidazole ring in 1 with a pyrrole ring in 2 makes the keto form in the latter more favored by 2 orders of magnitude (K-TAUT for 2 approximate to 10(3), as opposed to K-TAUT for 1 approximate to 10).

  DOI：

  10.1021/jo0497959

文献信息

• Artificial Genetic Systems:  Exploiting the “Aromaticity” Formalism To Improve the Tautomeric Ratio for Isoguanosine Derivatives
  作者：Theodore A. Martinot、Steven A. Benner

  DOI：10.1021/jo0497959

  日期：2004.5.1

  The tautomerism of 2'-deoxy-7-deaza-isoguanosine (2) was studied and compared to that of 2'-deoxyisoguanosine (1). The fixed N-1-methyl (8) and O-methyl (4) derivatives were synthesized to represent the pure extremes of each tautomer. The replacement of the imidazole ring in 1 with a pyrrole ring in 2 makes the keto form in the latter more favored by 2 orders of magnitude (K-TAUT for 2 approximate to 10(3), as opposed to K-TAUT for 1 approximate to 10).