2-benzamido-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine | 1360804-43-8

• 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-benzamido-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-benzamido-6-chloropurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 1360804-43-8
• 化学式: C₂₃H₂₂ClN₅O₈
• 分子量: 531.909
• InChiKey: CTMHMZPSWZDYJW-UVLLPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  氨基甲酸苄酯 、 2-benzamido-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以60%的产率得到[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-benzamido-6-(phenylmethoxycarbonylamino)purin-9-yl]oxolan-2-yl]methyl acetate
  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
• 作为产物：
  描述：

  2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三甲基溴硅烷 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 二溴甲烷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-benzamido-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine
  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