[(2R,3R,4R,5R)-5-[6-[acetyl(cyclopentyl)amino]purin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate | 266360-76-3

• 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: [(2R,3R,4R,5R)-5-[6-[acetyl(cyclopentyl)amino]purin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 266360-76-3
• 化学式: C₂₃H₂₉N₅O₈
• 分子量: 503.512
• InChiKey: AEERJXDBYZLTKS-ZDXOVATRSA-N

物化性质

• 沸点：
  657.0±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-[6-[acetyl(cyclopentyl)amino]purin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate 在 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到[(2R,3R,4R,5R)-5-[6-[acetyl(cyclopentyl)amino]-2-nitropurin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

  摘要：

  Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02271-6
• 作为产物：
  描述：

  N6-环戊基腺苷酸 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以70%的产率得到[(2R,3R,4R,5R)-5-[6-[acetyl(cyclopentyl)amino]purin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate
  参考文献：
  名称：

  2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes

  摘要：

  The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N-6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A(1), A(2A) and A(3) adenosine receptor subtypes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00415-7