2,3,5-O-tribenzoyl-1-O-ethyl-β-D-ribofuranose | 52783-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-O-tribenzoyl-1-O-ethyl-β-D-ribofuranose
• 英文别名: 1-O-Ethyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-ethoxyoxolan-2-yl]methyl benzoate
• CAS: 52783-88-7
• 化学式: C₂₈H₂₆O₈
• 分子量: 490.51
• InChiKey: UYUDIHUVDZOWAW-CBUXHAPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,5-O-tribenzoyl-1-O-ethyl-β-D-ribofuranose 生成 [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4,5-diacetylimidazol-1-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  FISCHER, U.;WYSS, P. -C.

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 乙醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以100%的产率得到2,3,5-O-tribenzoyl-1-O-ethyl-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis of small interfering RNAs containing acetal-type nucleoside analogs at their 3′-ends and analysis of their silencing activity and their ability to bind to the Argonaute2 PAZ domain

  摘要：

  In this study, we aimed to create small interfering RNAs (siRNAs) with increased silencing activities and nuclease resistance properties. Therefore, we designed and synthesized five types of siRNA containing acetal-type nucleoside analogs at their 3'-dangling ends. We found that the siRNA containing 1-O-(2,2,2-trifluoroethyl)-beta-D-ribofuranose at the 3'-dangling end was the most potent among the synthesized siRNAs and showed more resistance to nucleolytic degradation by a 3' exonuclease than a natural RNA did. Thus, modification of siRNAs by addition of 1-O-(2,2,2-trifluoroethyl)-beta-D-ribofuranose may hold promise as a means of improving the silencing activity and nuclease resistance of siRNAs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.011