1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose | 1354936-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose
• 英文别名: 2,2,2-trifluoroethyl β-D-ribofuranoside；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(2,2,2-trifluoroethoxy)oxolane-3,4-diol
• CAS: 1354936-06-3
• 化学式: C₇H₁₁F₃O₅
• 分子量: 232.157
• InChiKey: KZUKKTPKNVYYKB-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose 在 吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 2-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)]phosphanyl-1-O-(2,2,2-trifluoroethyl)-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
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以60%的产率得到1-O-(2,2,2-trifluoroethyl)-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

文献信息

• Direct Glycosylation of Unprotected and Unactivated Carbohydrates under Mild Conditions
  作者：Matthias Pfaffe、Rainer Mahrwald

  DOI：10.1021/ol203329u

  日期：2012.2.3

  Ligand exchange acetalization of acetals in the presence of catalytic amounts of mandelic acid and titanium tert-butoxide is reported. This transformation is successfully extended to glycosylation of unprotected and unactivated pentoses. Even unreactive pentoses such as d-arabinose or d-lyxose can be transformed by this new methodology into corresponding isopropyl glycosides.

  据报道，在催化量的扁桃酸和叔丁醇钛存在下，乙缩醛的配体交换缩醛化。该转化成功地扩展到未保护和未激活的戊糖的糖基化。甚至不反应的戊糖，例如d-阿拉伯糖或d- lyxose，也可以通过这种新方法转化为相应的异丙基糖苷。
• Organocatalyzed Direct Glycosylation of Unprotected and Unactivated Carbohydrates
  作者：Sebastian Schmalisch、Rainer Mahrwald

  DOI：10.1021/ol402914v

  日期：2013.11.15

  Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.