6-(piperidin-1-yl)-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine | 1018979-30-0

• 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: 6-(piperidin-1-yl)-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine
• 英文别名: tert-butyl-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(6-piperidin-1-ylpurin-9-yl)oxolan-3-yl]oxy-dimethylsilane
• CAS: 1018979-30-0
• 化学式: C₂₇H₄₉N₅O₃Si₂
• 分子量: 547.889
• InChiKey: YEYHAWKGBJOMBB-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  哌啶 、 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine 在 碘 、 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以65%的产率得到6-(piperidin-1-yl)-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  使用原位生产的六烷基磷三酰胺合成 N6,N6-二烷基腺嘌呤核苷

  摘要：

  仲胺与三氯化磷 (PCl3) 之间的反应导致形成相应的三（二烷基氨基）膦或六烷基磷三酰胺 [HAPT: (R2N)3P]。甲硅烷基保护的 2'-脱氧肌苷和乙酰基保护的肌苷与原位形成的 HAPT 和碘 (I2) 的反应导致形成 N6,N6-二烷基腺苷和 2'-脱氧腺苷。在某些情况下，胺的化学计量与叔胺碱的使用一样重要。通过 31 P{1H} NMR 研究了胺化学计量对 HAPT 与 I2 反应的影响。

  DOI：

  10.1002/ejoc.200800752

文献信息

• A Novel Polymer Supported Approach to Nucleoside Modification
  作者：Suyeal Bae、Mahesh K. Lakshman

  DOI：10.1021/jo702558n

  日期：2008.5.1

  Polymer-supported O-6-(benzotriazol-1-yl)inosine derivatives (Pol-I and Pol-dI) have been synthesized reasonably effectively via reaction of nucleoside phosphonium salts with polymer-linked HOBt (Pol-HOBt). In constast to solution chemistry, use of polymer-supported BOP (Pol-BOP) did not lead to efficient nucleoside loading. Presence of the nucleosides on the support could be readily detected by MAS NMR. Exposure of the polymer-supported nucleosides, Pol-I and Pol-dI, to alcohol, phenol, thiol and amine nucleophiles caused cleavage from the support leading directly to the C-6 modified nucleoside analogues. To our knowledge, these are the first examples of the application of such technology for nucleoside modification. Where possible, results of reactions with the polymer-supported nucleosides are compared to those from solution chemistry, providing insight into the differences between the two techniques. These new polymer-supported nucleosides can be conveniently utilized for diversity-oriented synthesis.
• Synthesis of N6,N6-Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ
  作者：Mahesh K. Lakshman、Asad Choudhury、Suyeal Bae、Eliezer Rochttis、Padmanava Pradhan、Amit Kumar

  DOI：10.1002/ejoc.200800752

  日期：——

  Reactions between secondary amines and phosphorus trichloride (PCl3) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R2N)3P]. Reaction of silyl-protected 2'-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT and iodine (I2) leads to the formation of N6,N6-dialkyl adenosine and 2'-deoxyadenosine. In some cases the

  仲胺与三氯化磷 (PCl3) 之间的反应导致形成相应的三（二烷基氨基）膦或六烷基磷三酰胺 [HAPT: (R2N)3P]。甲硅烷基保护的 2'-脱氧肌苷和乙酰基保护的肌苷与原位形成的 HAPT 和碘 (I2) 的反应导致形成 N6,N6-二烷基腺苷和 2'-脱氧腺苷。在某些情况下，胺的化学计量与叔胺碱的使用一样重要。通过 31 P1H} NMR 研究了胺化学计量对 HAPT 与 I2 反应的影响。