2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-(3-trifluoroacetamidoprop-1-ynyl)uridine | 1251827-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-(3-trifluoroacetamidoprop-1-ynyl)uridine
• CAS: 1251827-60-7
• 化学式: C₃₈H₃₈F₃N₃O₁₀
• 分子量: 753.729
• InChiKey: TVMGGEGITRHWKX-UKNNOAMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  159.57
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-(3-trifluoroacetamidoprop-1-ynyl)uridine 、 chloro-(2-cyanoethyl)-diisopropylaminophosphane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到2'-O-(2-methoxyethyl)-3'-O-(2-cyanoethyl(diisopropylamino)phosphanyl)-5'-O-(4,4'-dimethoxytrityl)-5-(3-trifluoroacetamidoprop-1-ynyl)uridine
  参考文献：
  名称：

  Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

  摘要：

  2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from D-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.005
• 作为产物：
  描述：

  2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine 、 N-三氟乙酰基炔丙基胺 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-(3-trifluoroacetamidoprop-1-ynyl)uridine
  参考文献：
  名称：

  Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

  摘要：

  2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from D-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.005