5′-O-(4,4′-dimethoxytrityl)-5-(1-(3-((2,2,2-trifluoroacetamido)methyl)phenyl)-1,2,3-triazol-4-yl)-2′-deoxyuridine | 1574218-80-6

• 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: 5′-O-(4,4′-dimethoxytrityl)-5-(1-(3-((2,2,2-trifluoroacetamido)methyl)phenyl)-1,2,3-triazol-4-yl)-2′-deoxyuridine
• CAS: 1574218-80-6
• 化学式: C₄₁H₃₇F₃N₆O₈
• 分子量: 798.775
• InChiKey: PNKLAASKRVIATK-LIVOIKKVSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  171.82
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5′-O-(4,4′-dimethoxytrityl)-5-(1-(3-((2,2,2-trifluoroacetamido)methyl)phenyl)-1,2,3-triazol-4-yl)-2′-deoxyuridine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54%的产率得到3′-O-(P-(2-cyanoethoxy)(N,N-diisopropylamino)phosphinyl)-5′-O-(4,4′-dimethoxytrityl)-5-(1-(3-((2,2,2-trifluoroacetamido)methyl)phenyl)-1,2,3-triazol-4-yl)-2′-deoxyuridine
  参考文献：
  名称：

  High-Affinity RNA Targeting by Oligonucleotides Displaying Aromatic Stacking and Amino Groups in the Major Groove. Comparison of Triazoles and Phenyl Substituents

  摘要：

  Three 5-modified 2'-deoxyuridine nucleosides were synthesized and incorporated into oligonucleotides and compared with the previously published 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine monomer W. The introduction of an aminomethyl group on the phenyl group led to monomer X, which was found to thermally stabilize a 9-mer DNA:RNA duplex, presumably through the partial neutralization of the negative charge of the backbone. By also taking advantage of the stacking interactions in the major groove of two or more of the monomer X, an extremely high thermal stability was obtained. A regioisomer of the phenyltriazole substituent, that is the 5-(4-phenyl-1,2,3-triazol-1-yl)-2'-deoxyuridine monomer Y, was found to destabilize the DNA:RNA duplex significantly, but stacking in the major groove compensated for this when two to four monomers were incorporated consecutively. Finally, the 5-phenyl-2'-deoxyuridine monomer Z was incorporated for comparison, and it was found to give a more neutral influence on duplex stability indicating less efficient stacking interactions. The duplexes were investigated by CD spectroscopy and MD simulations.

  DOI：

  10.1021/jo4025896
• 作为产物：
  描述：

  3-溴苄胺 在 copper(l) iodide 、 sodium azide 、 sodium ascorbate 、 N,N-二甲基乙二胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成 5′-O-(4,4′-dimethoxytrityl)-5-(1-(3-((2,2,2-trifluoroacetamido)methyl)phenyl)-1,2,3-triazol-4-yl)-2′-deoxyuridine
  参考文献：
  名称：

  High-Affinity RNA Targeting by Oligonucleotides Displaying Aromatic Stacking and Amino Groups in the Major Groove. Comparison of Triazoles and Phenyl Substituents

  摘要：

  Three 5-modified 2'-deoxyuridine nucleosides were synthesized and incorporated into oligonucleotides and compared with the previously published 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine monomer W. The introduction of an aminomethyl group on the phenyl group led to monomer X, which was found to thermally stabilize a 9-mer DNA:RNA duplex, presumably through the partial neutralization of the negative charge of the backbone. By also taking advantage of the stacking interactions in the major groove of two or more of the monomer X, an extremely high thermal stability was obtained. A regioisomer of the phenyltriazole substituent, that is the 5-(4-phenyl-1,2,3-triazol-1-yl)-2'-deoxyuridine monomer Y, was found to destabilize the DNA:RNA duplex significantly, but stacking in the major groove compensated for this when two to four monomers were incorporated consecutively. Finally, the 5-phenyl-2'-deoxyuridine monomer Z was incorporated for comparison, and it was found to give a more neutral influence on duplex stability indicating less efficient stacking interactions. The duplexes were investigated by CD spectroscopy and MD simulations.

  DOI：

  10.1021/jo4025896