1-(3-amino-2,3,6-trideoxy-α-L-arabino-hexofuranosyl)thymine | 136035-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3-amino-2,3,6-trideoxy-α-L-arabino-hexofuranosyl)thymine
• 英文别名: Amino nucleoside；1-[(2R,4S,5R)-4-amino-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 136035-14-8
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: FAXNJWRNLCWHMW-MAUMQABQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 mercury(II) sulfate 、 甲胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 10.25h， 生成 1-(3-amino-2,3,6-trideoxy-α-L-arabino-hexofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Evaluation of Antiviral Activity of L-Acosamine and L-Ristosamine Nucleosides of Furanose Configuration.

  摘要：

  Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.

  DOI：

  10.3891/acta.chem.scand.45-0616

文献信息

• LAU, JESPER;PEDERSEN, ERIK B.;NIELSEN, CARSTEN M., ACTA CHEM. SCAND., 45,(1991) N, C. 616-620
  作者：LAU, JESPER、PEDERSEN, ERIK B.、NIELSEN, CARSTEN M.

  DOI：——

  日期：——
• Synthesis and Evaluation of Antiviral Activity of L-Acosamine and L-Ristosamine Nucleosides of Furanose Configuration.
  作者：Jesper Lau、Erik B. Pedersen、Carsten M. Nielsen、Jorma Korvola、Kari Leskinen、I. Trabjerg

  DOI：10.3891/acta.chem.scand.45-0616

  日期：——

  Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.