N⁶-benzoyl-9-[2-deoxy-4-thio-β-D-ribofuranosyl]adenine | 51094-97-4

• 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: N⁶-benzoyl-9-[2-deoxy-4-thio-β-D-ribofuranosyl]adenine
• 英文别名: N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]purin-6-yl]benzamide
• CAS: 51094-97-4
• 化学式: C₁₇H₁₇N₅O₃S
• 分子量: 371.42
• InChiKey: JPUSIDQKETZYKW-YNEHKIRRSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-9-[2-deoxy-4-thio-β-D-ribofuranosyl]adenine 在 甲胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以47%的产率得到2'-deoxy-4'-thioadenosine
  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：

  N⁶-benzoyl-9-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]adenine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到N⁶-benzoyl-9-[2-deoxy-4-thio-β-D-ribofuranosyl]adenine
  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.