5-acetyl-2-amino-3-[3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-β-D-ribofuranosyl]-1H-pyrrole | 948852-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-2-amino-3-[3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-β-D-ribofuranosyl]-1H-pyrrole
• 英文别名: 1-[5-amino-4-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1H-pyrrol-2-yl]ethanone
• CAS: 948852-38-8
• 化学式: C₂₃H₄₄N₂O₄Si₂
• 分子量: 468.784
• InChiKey: NDPOVDHDENUKAU-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetyl-2-amino-3-[3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-β-D-ribofuranosyl]-1H-pyrrole 在 三氟甲磺酸三甲基硅酯 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以84%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：

  5-acetyl-3-[3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-β-D-ribofuranosyl]-2-nitro-1H-pyrrole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到5-acetyl-2-amino-3-[3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-β-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

文献信息

• Synthesis of 5-acetyl-2-aminopyrrole C-deoxyribonucleoside
  作者：Hiroshi Oda、Takeshi Hanami、Takashi Iwashita、Miki Kojima、Masayoshi Itoh、Yoshihide Hayashizaki

  DOI：10.1016/j.tet.2007.09.082

  日期：2007.12

  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.