N2-(N,N-dimethylaminomethylidene)-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]guanine | 869347-17-1

• 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-(N,N-dimethylaminomethylidene)-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]guanine
• 英文别名: N²-(N,N-dimethylaminomethylidene)-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]guanine
• CAS: 869347-17-1
• 化学式: C₂₅H₄₄N₆O₅SSi₂
• 分子量: 596.899
• InChiKey: DJURFCLOIZSCBE-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  127.09
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N2-(N,N-dimethylaminomethylidene)-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]guanine 在 4-二甲氨基吡啶 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 N2-(N,N-dimethylaminomethylidene)-9-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-arabinofuranosyl]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
• 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 、 1,3二氯-1,1,3,3-四异丙基二硅氧烷 在 吡啶 作用下， 反应 3.5h， 以78%的产率得到N2-(N,N-dimethylaminomethylidene)-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-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