1-(3-deoxy-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-(3-deoxy-β-L-erythro-pentofuranosyl)thymine
• 英文别名: 1-(3-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione；1-[(2S,3S,5R)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: UYUWZFRYAAHPDN-FJXKBIBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

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 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 1-(3-deoxy-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 3'-Deoxy-β-L-erythro-pentofuranosyl Nucleosides of the Five Naturally Occurring Nucleic Acid Bases
  作者：C. Mathé、G. Gosselin、M. -C. Bergogne、A. -M. Aubertin、G. Obert、A. Kirn、J. -L. Imbach

  DOI：10.1080/15257779508012424

  日期：1995.5.1

  of the protecting groups. All the prepared compounds were tested for their ability to inhibit the replication of a variety of DNA and RNA viruses (including HIV), but they did not show significant antiviral activity.

  摘要迄今未知的标题化合物是通过嘧啶和嘌呤苷元与适当的过酰基化的3'-脱氧-β-L-赤型戊呋喃糖进行糖基化立体立体合成的，然后除去保护基团。测试了所有制备的化合物抑制多种DNA和RNA病毒（包括HIV）复制的能力，但它们未显示出显着的抗病毒活性。
• 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.