N²-(N,N-dimethylaminomethylidene)-9-[2-deoxy-4-thio-β-D-ribofuranosyl]guanine | 869347-22-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: N²-(N,N-dimethylaminomethylidene)-9-[2-deoxy-4-thio-β-D-ribofuranosyl]guanine
• 英文别名: N'-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 869347-22-8
• 化学式: C₁₃H₁₈N₆O₃S
• 分子量: 338.39
• InChiKey: NARICTGVIOWSQT-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N²-(N,N-dimethylaminomethylidene)-9-[2-deoxy-4-thio-β-D-ribofuranosyl]guanine 在 氨 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以50%的产率得到2'-deoxy-4'-thioguanosine
  参考文献：
  名称：

  Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA

  摘要：

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.

  DOI：

  10.1021/jo051248f
• 作为产物：
  描述：

  N'-[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲氧基异庚腈 、 四丁基氟化铵 、 四丁基溴化铵 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 3.5h， 生成 N²-(N,N-dimethylaminomethylidene)-9-[2-deoxy-4-thio-β-D-ribofuranosyl]guanine
  参考文献：
  名称：

  Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA

  摘要：

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.

  DOI：

  10.1021/jo051248f

文献信息

• Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA
  作者：Naonori Inoue、Daisuke Kaga、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/jo051248f

  日期：2005.10.1

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.