4-amino-6-chloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine | 220249-21-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4-amino-6-chloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
• 英文别名: (2S,3R,5S)-2-(4-amino-6-chloroimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 220249-21-8
• 化学式: C₁₁H₁₃ClN₄O₃
• 分子量: 284.702
• InChiKey: YOHFWBLJUQIJRX-MJIFXRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-6-chloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以65%的产率得到4-amino-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  Synthesis of New 3′-Deoxyribonucleosides Employing the Acid-Catalyzed Fusion Method

  摘要：

  Coupling of 4,6-dichloro-1H-imidazo[4,5-c]pyridine (2.6-dichloro-3-deaza-9H-purine) (I) with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose (2), employing the acid-catalyzed fusion method, is reported (Scheme I). The condensation reaction was regioselective and gave the three N-1-glycosylation products 3-5, whereas no N-3-nucleosides were detected. Treatment of 3-5 with methanolic ammonia afforded the corresponding deprotected nucleosides 6-8. Compounds 6 and 7 were assigned the structure of the beta-D- and alpha-D-anomeric N-1-(3'-deoxyribo)nucleosides, respectively. The third derivative 8 proved to be the alpha-D-anomer of a 3'-deoxyarabinonucleoside deriving from epimerization at C(2) of the sugar. The 2-chloro- and N-6-substituted derivatives 9, 11, and 13 of 3'-decxy-3-deazaadenosine (10) and of its alpha-D-anomer 12 can be obtained from these versatile synthons (Schemes 2 and 3).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2326::aid-hlca2326>3.0.co;2-4
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose 在 镍 氨 、 对甲苯磺酸 、 一水合肼 作用下， 以 水 为溶剂， 25.0~160.0 ℃ 、3.33 kPa 条件下， 反应 30.08h， 生成 4-amino-6-chloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  Synthesis of New 3′-Deoxyribonucleosides Employing the Acid-Catalyzed Fusion Method

  摘要：

  Coupling of 4,6-dichloro-1H-imidazo[4,5-c]pyridine (2.6-dichloro-3-deaza-9H-purine) (I) with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose (2), employing the acid-catalyzed fusion method, is reported (Scheme I). The condensation reaction was regioselective and gave the three N-1-glycosylation products 3-5, whereas no N-3-nucleosides were detected. Treatment of 3-5 with methanolic ammonia afforded the corresponding deprotected nucleosides 6-8. Compounds 6 and 7 were assigned the structure of the beta-D- and alpha-D-anomeric N-1-(3'-deoxyribo)nucleosides, respectively. The third derivative 8 proved to be the alpha-D-anomer of a 3'-deoxyarabinonucleoside deriving from epimerization at C(2) of the sugar. The 2-chloro- and N-6-substituted derivatives 9, 11, and 13 of 3'-decxy-3-deazaadenosine (10) and of its alpha-D-anomer 12 can be obtained from these versatile synthons (Schemes 2 and 3).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2326::aid-hlca2326>3.0.co;2-4