5′-O-(4,4′-dimethoxytrityl)-4′-C-[(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine | 1593481-27-6

• 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)-4′-C-[(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-5-[[4-(trifluoromethyl)triazol-1-yl]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1593481-27-6
• 化学式: C₃₅H₃₄F₃N₅O₇
• 分子量: 693.679
• InChiKey: KQUFQJDZNAYFSO-AARCXHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5′-O-(4,4′-dimethoxytrityl)-4′-C-[(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到3′-O-[(2-cyanoethoxy)-(N,N-diisopropylamino)phosphinyl]-5′-O-(4,4′-dimethoxytrityl)-4′-C-[(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine
  参考文献：
  名称：

  4′-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine as a Sensitive ¹⁹F NMR Sensor for the Detection of Oligonucleotide Secondary Structures

  摘要：

  4'-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine was synthesized and incorporated as a phosphoramidite into oligonucleotide sequences. Its applicability as a sensor for the F-19 NMR spectroscopic detection of DNA and RNA secondary structures was demonstrated. On DNA, the F-19 NMR measurements were focused on monitoring of duplex-triplex conversion, for which this fluorine-labeled 2'-deoxynucleoside proved to be a powerful sensor. This sensor seemingly favors DNA, but its behavior in the RNA environment also turned out to be informative. As a demonstration, invasion of a 2'-O-methyl oligoribonucleotide into an RNA hairpin model (HIV-1 TAR) was monitored by F-19 NMR spectroscopy. According to the thermal denaturation studies by UV spectroscopy, the effect of the 4'-C-(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl moiety on the stability of these DNA and RNA models was marginal.

  DOI：

  10.1021/jo500326j
• 作为产物：
  描述：

  3,3,3-三氟-1-丙炔 、 4′-cazidomethyl-5′-O-(4,4′-dimethoxytrityl)thymidine 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以77%的产率得到5′-O-(4,4′-dimethoxytrityl)-4′-C-[(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine
  参考文献：
  名称：

  4′-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine as a Sensitive ¹⁹F NMR Sensor for the Detection of Oligonucleotide Secondary Structures

  摘要：

  4'-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine was synthesized and incorporated as a phosphoramidite into oligonucleotide sequences. Its applicability as a sensor for the F-19 NMR spectroscopic detection of DNA and RNA secondary structures was demonstrated. On DNA, the F-19 NMR measurements were focused on monitoring of duplex-triplex conversion, for which this fluorine-labeled 2'-deoxynucleoside proved to be a powerful sensor. This sensor seemingly favors DNA, but its behavior in the RNA environment also turned out to be informative. As a demonstration, invasion of a 2'-O-methyl oligoribonucleotide into an RNA hairpin model (HIV-1 TAR) was monitored by F-19 NMR spectroscopy. According to the thermal denaturation studies by UV spectroscopy, the effect of the 4'-C-(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl moiety on the stability of these DNA and RNA models was marginal.

  DOI：

  10.1021/jo500326j

文献信息

• 4′-<i>C</i>-[(4-Trifluoromethyl-1<i>H</i>-1,2,3-triazol-1-yl)methyl]thymidine as a Sensitive ¹⁹F NMR Sensor for the Detection of Oligonucleotide Secondary Structures
  作者：Lotta Granqvist、Pasi Virta

  DOI：10.1021/jo500326j

  日期：2014.4.18

  4'-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine was synthesized and incorporated as a phosphoramidite into oligonucleotide sequences. Its applicability as a sensor for the F-19 NMR spectroscopic detection of DNA and RNA secondary structures was demonstrated. On DNA, the F-19 NMR measurements were focused on monitoring of duplex-triplex conversion, for which this fluorine-labeled 2'-deoxynucleoside proved to be a powerful sensor. This sensor seemingly favors DNA, but its behavior in the RNA environment also turned out to be informative. As a demonstration, invasion of a 2'-O-methyl oligoribonucleotide into an RNA hairpin model (HIV-1 TAR) was monitored by F-19 NMR spectroscopy. According to the thermal denaturation studies by UV spectroscopy, the effect of the 4'-C-(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl moiety on the stability of these DNA and RNA models was marginal.