N²,O^3',O^5'-triacetyl-2'-deoxy-2'-fluoroguanosine | 134444-76-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²,O^3',O^5'-triacetyl-2'-deoxy-2'-fluoroguanosine
• 英文别名: [(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-1H-purin-9-yl)-3-acetyloxy-4-fluorooxolan-2-yl]methyl acetate
• CAS: 134444-76-1
• 化学式: C₁₆H₁₈FN₅O₇
• 分子量: 411.347
• InChiKey: VAFZHUOHSVMVIB-NDLNZWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N²,O^3',O^5'-triacetyl-2'-deoxy-2'-fluoroguanosine 在 吡啶 、 四氮唑 、 sodium hydroxide 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.17h， 生成 [(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479
• 作为产物：
  描述：

  sodium acetate 、 N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine 以 乙酸酐 、 溶剂黄146 为溶剂， 以80%的产率得到N²,O^3',O^5'-triacetyl-2'-deoxy-2'-fluoroguanosine
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479

文献信息

• Antiviral compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0417999B1

  公开（公告）日：1996-03-13
• US5420115A
  申请人：——

  公开号：US5420115A

  公开（公告）日：1995-05-30