6-Amino-9-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-3,9-dihydro-purin-2-one | 181508-25-8

• 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: 6-Amino-9-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-3,9-dihydro-purin-2-one
• 英文别名: 6-amino-9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-purin-2-one
• CAS: 181508-25-8
• 化学式: C₁₀H₁₁N₅O₃
• 分子量: 249.229
• InChiKey: HOYLPWQXGFUVME-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Amino-9-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-3,9-dihydro-purin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以83%的产率得到2',3'-dideoxyisoguanosine
  参考文献：
  名称：

  Nucleosides VIII:¹Synthesis of 2′, 3′-Dideoxy- and 2′, 3′-Didehydro-2′, 3′-Di Deoxyisoguanosine as Potential Antiretroviral Agents

  摘要：

  2',3'-Didehydro-2',3'-dideoxyisoguanosin (2) and 2',3'-dideoxyisoguanosine (3) have been synthesized by utilizing the Corey-Winter approach starting from isoguanosine. The 6-amino and 5'-hydroxy biprotected isoguanosine derivative was converted to the corresponding 2',3'-thionocarbonate, which was heated with triethyl phosphite to afford the 2',3'-olefinic product. Either a tert-butyldimethylsilyl or a 4,4'-dimethoxytrityl group was used in the protection of 5'-hydroxy function. Compounds 2 and 3 were found inactive against human immunodeficiency virus (HIV), human cytomegalovirus (HCMV), and herpes simplex virus type 1 (HSV-1).

  DOI：

  10.1080/07328319608002427
• 作为产物：
  描述：

  N'-(9-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-3,9-dihydro-2H-purin-6-yl)-N,N-dimethyl-formamidine 在 氨 、 水 、 silica gel 、 亚磷酸三乙酯 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 145.0h， 生成 6-Amino-9-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-3,9-dihydro-purin-2-one
  参考文献：
  名称：

  Nucleosides VIII:¹Synthesis of 2′, 3′-Dideoxy- and 2′, 3′-Didehydro-2′, 3′-Di Deoxyisoguanosine as Potential Antiretroviral Agents

  摘要：

  2',3'-Didehydro-2',3'-dideoxyisoguanosin (2) and 2',3'-dideoxyisoguanosine (3) have been synthesized by utilizing the Corey-Winter approach starting from isoguanosine. The 6-amino and 5'-hydroxy biprotected isoguanosine derivative was converted to the corresponding 2',3'-thionocarbonate, which was heated with triethyl phosphite to afford the 2',3'-olefinic product. Either a tert-butyldimethylsilyl or a 4,4'-dimethoxytrityl group was used in the protection of 5'-hydroxy function. Compounds 2 and 3 were found inactive against human immunodeficiency virus (HIV), human cytomegalovirus (HCMV), and herpes simplex virus type 1 (HSV-1).

  DOI：

  10.1080/07328319608002427