1-<2-deoxy-β-D-erythro-pentofuranosyl>-3-iodo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine | 220906-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-<2-deoxy-β-D-erythro-pentofuranosyl>-3-iodo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine
• 英文别名: (2R,3S,5R)-5-(6-amino-3-iodo-4-propoxypyrazolo[3,4-d]pyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 220906-59-2
• 化学式: C₁₃H₁₈IN₅O₄
• 分子量: 435.222
• InChiKey: WGXFWKLQHVOLSK-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-<2-deoxy-β-D-erythro-pentofuranosyl>-3-iodo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine 在 sodium hydroxide 作用下， 以87%的产率得到6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides

  摘要：

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3
• 作为产物：
  描述：

  1-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-3-iodo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine 在 NaOPr 作用下， 以 丙醇 为溶剂， 反应 2.0h， 以78%的产率得到1-<2-deoxy-β-D-erythro-pentofuranosyl>-3-iodo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine
  参考文献：
  名称：

  TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides

  摘要：

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3