2,2,2-Trifluoro-N-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylamino]-ethyl}-acetamide | 854933-33-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2,2,2-Trifluoro-N-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylamino]-ethyl}-acetamide
• CAS: 854933-33-8
• 化学式: C₁₃H₁₇F₃N₄O₅
• 分子量: 366.297
• InChiKey: RQDPADCNZGPUDZ-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.03
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125.71
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylamino]-ethyl}-acetamide 在 吡啶 、 四氮唑 作用下， 以 乙腈 为溶剂， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-{2-oxo-4-[2-(2,2,2-trifluoro-acetylamino)-ethylamino]-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Phototriggering of Caged Fluorescent Oligodeoxynucleotides

  摘要：

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.

  DOI：

  10.1021/ol047729n
• 作为产物：
  描述：

  N-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-4-methyl-benzenesulfonamide 在 吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2,2,2-Trifluoro-N-{2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylamino]-ethyl}-acetamide
  参考文献：
  名称：

  Phototriggering of Caged Fluorescent Oligodeoxynucleotides

  摘要：

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.

  DOI：

  10.1021/ol047729n