[(6aR,8R,9R,9aS)-8-(6-benzamidopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate | 869347-16-0

• 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: [(6aR,8R,9R,9aS)-8-(6-benzamidopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate
• CAS: 869347-16-0
• 化学式: C₃₀H₄₂F₃N₅O₇S₂Si₂
• 分子量: 761.991
• InChiKey: PTWURSNGHRFITH-UQCYUJMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(6aR,8R,9R,9aS)-8-(6-benzamidopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate 在 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 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 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：

  (6aR,8R,9R,9aS)-8-(6-aminopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 9.67h， 生成 [(6aR,8R,9R,9aS)-8-(6-benzamidopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate
  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.