Benzoic acid 4-(6-chloro-purin-9-yl)-2,5-dihydro-furan-3-ylmethyl ester | 467249-36-1

• 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: Benzoic acid 4-(6-chloro-purin-9-yl)-2,5-dihydro-furan-3-ylmethyl ester
• CAS: 467249-36-1
• 化学式: C₁₇H₁₃ClN₄O₃
• 分子量: 356.768
• InChiKey: FMIMLPJOPYFWRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid 4-(6-chloro-purin-9-yl)-2,5-dihydro-furan-3-ylmethyl ester 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 (+/-)-cis-6-amino-9-(4-hydroxymethyltetrahydrofuran-3-yl)purine
  参考文献：
  名称：

  Nucleosides with furanyl scaffolds

  摘要：

  Synthesis of purine and pyrimidine nucleosides with furanyl scaffolds is described. The 2-functionalized tetrahydrofuranol derivatives 12 and 15 were coupled with nucleobases through the Mitsunobu reaction. The methodology developed is general and can also be applied for an efficient synthesis of apionucleosides. In addition, the methodology was used for the synthesis of the unsaturated purine nucleoside 22. However, when the elimination reaction used to produce 22 was applied to the pyrimidine case, the stable anhydro compound 24 was produced. The structures of 18 and 22 were confirmed by single-crystal X-ray data. Antiviral evaluation was performed. 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00430-1
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)tetrahydro-4-methylidenefuran 在 吡啶 、 氟化铵 、 四氧化锇 、 四丁基氟化铵 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 39.5h， 生成 Benzoic acid 4-(6-chloro-purin-9-yl)-2,5-dihydro-furan-3-ylmethyl ester
  参考文献：
  名称：

  Nucleosides with furanyl scaffolds

  摘要：

  Synthesis of purine and pyrimidine nucleosides with furanyl scaffolds is described. The 2-functionalized tetrahydrofuranol derivatives 12 and 15 were coupled with nucleobases through the Mitsunobu reaction. The methodology developed is general and can also be applied for an efficient synthesis of apionucleosides. In addition, the methodology was used for the synthesis of the unsaturated purine nucleoside 22. However, when the elimination reaction used to produce 22 was applied to the pyrimidine case, the stable anhydro compound 24 was produced. The structures of 18 and 22 were confirmed by single-crystal X-ray data. Antiviral evaluation was performed. 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00430-1