(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzyloxy)-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate | 1360804-45-0

• 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: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzyloxy)-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 1360804-45-0
• 化学式: C₂₃H₂₃IN₄O₈
• 分子量: 610.362
• InChiKey: JGWKTRMBTRMYLU-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  140.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzyloxy)-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 、 苯甲酰胺 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 1,4-二氧六环 、 甲苯 为溶剂， 反应 36.0h， 以95%的产率得到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
• 作为产物：
  描述：

  2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 copper(l) iodide 、 二碘甲烷 、 碘 、 sodium hydride 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzyloxy)-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  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