1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine | 136035-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine
• 英文别名: L-Acosamine nucleoside；[(1S)-1-[(2R,3R,5R)-3-(1,3-dioxoisoindol-2-yl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethyl] acetate
• CAS: 136035-09-1
• 化学式: C₂₁H₂₁N₃O₇
• 分子量: 427.414
• InChiKey: GJKVGHBACKLCOR-QYHDQYMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine 在 甲胺 作用下， 以 乙醇 为溶剂， 以83%的产率得到1-(3-amino-2,3,6-trideoxy-α-L-ribo-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
• 作为产物：
  描述：

  5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-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：——