2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine | 1234319-81-3

• 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: 2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-benzamido-6-phenylmethoxypurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 1234319-81-3
• 化学式: C₃₀H₂₉N₅O₉
• 分子量: 603.588
• InChiKey: YIAGVBMSJROYGJ-UQCYUJMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以95%的产率得到2-N-benzoyl-2',3',5'-tri-O-acetylguanosine
  参考文献：
  名称：

  ¹⁵N Double-Labeled Guanosine from Inosine through Ring-Opening−Ring-Closing and One-Pot Pd-Catalyzed C−O and C−N Cross-Coupling Reactions

  摘要：

  [N,1-N-15(2)]-Guanosine, or [1,NH2-N-15(2)]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with (NH2OH)-N-15, followed by conversion of the N-15-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and (PhCONH2)-N-15 or (PrCONH2)-Pr-i-N-15 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.

  DOI：

  10.1021/jo100808w
• 作为产物：
  描述：

  2',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium hydride 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 36.0h， 生成 2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine
  参考文献：
  名称：

  Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0°C

  摘要：

  Pd-catalysed reactions of 2-Cl, 2-Br and 2-I derivatives of a 6-chloropurine nucleoside with benzamide have been compared, using Pd(2)dba(3), Xantphos and Cs2CO3 in toluene, between 20 and 80 degrees C. The reactivity order was 2-I > 2-Br > 6-Cl >> 2-Cl. The 2-I substituent could be replaced even at 0 degrees C, under conditions disclosed here for the first time. On the other hand, the replacement of the chlorine atom at position 2 (2-Cl) required 110 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.012