1-(2-azido-2,3-dideoxy-β-L-erythro-pentofuranosyl)thymine

• 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: 1-(2-azido-2,3-dideoxy-β-L-erythro-pentofuranosyl)thymine
• 英文别名: 1-(3-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione；1-[(2S,3S,5R)-3-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: GRAIAQOAALQBTB-FJXKBIBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose 在 ammonium sulfate 、 四甲基乙二胺 、 叠氮基三甲基硅烷 、 氨 、 sodium methylate 、 lithium fluoride 、 三苯基膦 、 六甲基二硅氮烷 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.25h， 生成 1-(2-azido-2,3-dideoxy-β-L-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of the β-L-Enantiomers of Some Thymine 3′-Deoxypentofuranonucleoside Derivatives

  摘要：

  3'-Deoxy-beta -L-erythro- (3), 3'-deoxy-beta -L-threo- (6), 2'-fluoro- (7) and 2'-azido-2',3'-dideoxy-beta -L-elythro- (10) pentofuranonucleoside derivatives of thymine have been synthesized and their antiviral properties examined. All these derivatives were stereospecifically prepared by glycosylation of thymine with a suitable peracylated 3-deoxy-L-elythro-pentofuranose sugar (1), followed by appropriate chemical modifications. The prepared compounds were tested for their activity against HIV, but they did not show an antiviral effect.

  DOI：

  10.1080/15257770008045443

文献信息

• Synthesis and Antiviral Evaluation of the β-L-Enantiomers of Some Thymine 3′-Deoxypentofuranonucleoside Derivatives
  作者：Christophe Mathé、Gilles Gosselin

  DOI：10.1080/15257770008045443

  日期：2000.10

  3'-Deoxy-beta -L-erythro- (3), 3'-deoxy-beta -L-threo- (6), 2'-fluoro- (7) and 2'-azido-2',3'-dideoxy-beta -L-elythro- (10) pentofuranonucleoside derivatives of thymine have been synthesized and their antiviral properties examined. All these derivatives were stereospecifically prepared by glycosylation of thymine with a suitable peracylated 3-deoxy-L-elythro-pentofuranose sugar (1), followed by appropriate chemical modifications. The prepared compounds were tested for their activity against HIV, but they did not show an antiviral effect.