5-acetyl-3-(2'-deoxy-β-D-ribofuranosyl)-2-nitro-1H-pyrrole | 948852-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-3-(2'-deoxy-β-D-ribofuranosyl)-2-nitro-1H-pyrrole
• 英文别名: 1-[4-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-nitro-1H-pyrrol-2-yl]ethanone
• CAS: 948852-36-6
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: QEEBSYNLBBBNTA-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-acetyl-3-(2'-deoxy-β-D-ribofuranosyl)-2-nitro-1H-pyrrole 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 反应 0.67h， 以46%的产率得到5-acetyl-2-amino-3-[2'-deoxy-α-D-ribofuranosyl]-1H-pyrrole
  参考文献：
  名称：

  Synthesis of 5-acetyl-2-aminopyrrole C-deoxyribonucleoside

  摘要：

  A novel C-deoxyribonucleoside bearing 2-aminopyrrole was synthesized. The C-glycosidation between deoxyribose and pyrrole ring was carried out using palladium-catalyzed Heck coupling in the presence of excess amount of lithium chloride as an additive. The synthesized aminopyrrole nucleoside is expected to become a promising counterpart of the artificial nucleoside pair. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.082
• 作为产物：
  描述：

  (2R,5R)-5-(5-acetyl-2-nitro-1H-pyrrol-3-yl)-2-hydroxymethyltetrahydrofuran-3-one 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以87%的产率得到5-acetyl-3-(2'-deoxy-β-D-ribofuranosyl)-2-nitro-1H-pyrrole
  参考文献：
  名称：

  Synthesis of 5-acetyl-2-aminopyrrole C-deoxyribonucleoside

  摘要：

  A novel C-deoxyribonucleoside bearing 2-aminopyrrole was synthesized. The C-glycosidation between deoxyribose and pyrrole ring was carried out using palladium-catalyzed Heck coupling in the presence of excess amount of lithium chloride as an additive. The synthesized aminopyrrole nucleoside is expected to become a promising counterpart of the artificial nucleoside pair. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.082