3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine | 215176-57-1

• 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'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine
• 英文别名: [(2S,3R,4R,5R)-4-acetyloxy-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 215176-57-1
• 化学式: C₁₉H₁₉N₅O₇
• 分子量: 429.389
• InChiKey: REXZBVHQTCLNQJ-KCYZZUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine 在 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 3'-deoxy-3'-(4-hydroxymethyl-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
• 作为产物：
  描述：

  5-O-benzoyl-α-D-xylofuranose 在 吡啶 、 sodium azide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 43.0h， 生成 3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-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

• Synthesis and Anti-HIV Activity of <i>β</i>-D-3′-Azido-2′,3′-unsaturated Nucleosides and <i>β</i>-D-3′-Azido-3′-deoxyribofuranosylnucleosides
  作者：Srinivas Gadthula、Chung K. Chu、Raymond F. Schinazi

  DOI：10.1080/15257770500267170

  日期：2005.9.1

  discovery of 3′-azido-3′-deoxythymidine (AZT) and 2′,3′-didehydro-2′,3′-dideoxythymidine (d4T) as potent and selective inhibitors of the replication of human immunodeficiency virus (HIV), there has been a growing interest for the synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides with electron withdrawing groups on the sugar moiety. Here we described an efficient method for the synthesis of such nucleoside

  自从发现 3'-azido-3'-deoxythymidine (AZT) 和 2',3'-didehydro-2',3'-dideoxythymidine (d4T) 作为人类免疫缺陷病毒 (HIV) 复制的有效和选择性抑制剂以来，人们对合成在糖部分具有吸电子基团的 2',3'-didehydro-2',3'-dideoxynucleoside 越来越感兴趣。在这里，我们描述了一种合成具有 AZT 和 d4T 结构特征的核苷类似物的有效方法。关键中间体 3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose, 5 由市售的 D-木糖分五步合成，其中一系列嘧啶和嘌呤核苷以高产率合成。使用适当的化学修饰将所得的受保护核苷转化为目标核苷。