3'-deoxy-3'-[4-(naphthyl-2-yloxymethylene)-1,2,3-triazol-1-yl]-5-methyluridine | 1519007-59-0

• 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: 3'-deoxy-3'-[4-(naphthyl-2-yloxymethylene)-1,2,3-triazol-1-yl]-5-methyluridine
• 英文别名: 1-[(2R,3R,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-[4-(naphthalen-2-yloxymethyl)triazol-1-yl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1519007-59-0
• 化学式: C₂₃H₂₃N₅O₆
• 分子量: 465.466
• InChiKey: AWBZGORETHVCNQ-NXLVEIQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-azido-5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 在 copper(l) iodide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 3'-deoxy-3'-[4-(naphthyl-2-yloxymethylene)-1,2,3-triazol-1-yl]-5-methyluridine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine

  摘要：

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.

  DOI：

  10.1080/15257770.2013.847957

文献信息

• Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine
  作者：Anu Arya、Divya Mathur、Abhilash Tyagi、Rajesh Kumar、Vinod Kumar、Carl E. Olsen、Rajendra K. Saxena、Ashok K. Prasad

  DOI：10.1080/15257770.2013.847957

  日期：2013.12.2

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.