N3-(p-methoxybenzyl)-thymin-1-ylacetyl fluoride | 388606-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N3-(p-methoxybenzyl)-thymin-1-ylacetyl fluoride
• 英文别名: 2-[3-[(4-Methoxyphenyl)methyl]-5-methyl-2,4-dioxopyrimidin-1-yl]acetyl fluoride
• CAS: 388606-56-2
• 化学式: C₁₅H₁₅FN₂O₄
• 分子量: 306.294
• InChiKey: QMIRKFRZYSGWJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N3-(p-methoxybenzyl)-thymin-1-ylacetyl fluoride 、 N-(4,4'-dimethoxytrityl)-ethanolamine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-acetyl-N-(acetamidoethyl)glycine 、 ((2-Acetylamino-ethyl)-{2-[3-(4-methoxy-benzyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-acetyl}-amino)-acetic acid
  参考文献：
  名称：

  Optimization of a Solid-Phase Synthesis of a PNA Monomer

  摘要：

  [GRAPHICS]A new scheme for the synthesis of peptide nucleic acid (PNA) is described. First, a resin-bound amino acid is alkylated under Fukuyama-Mitsunobu conditions. A nucleobase is then incorporated via an acid fluoride. Subsequently, oligomerization may be achieved by deprotection, coupling of another amino acid, and repetition of the cycle. Each step of the submonomer synthesis has been optimized to provide essentially quantitative yield.

  DOI：

  10.1021/ol016822y
• 作为产物：
  描述：

  1-(ethoxycarbonylmethyl)thymine 在 吡啶 、 sodium hydroxide 、 三聚氟氰 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 N3-(p-methoxybenzyl)-thymin-1-ylacetyl fluoride
  参考文献：
  名称：

  Optimization of a Solid-Phase Synthesis of a PNA Monomer

  摘要：

  [GRAPHICS]A new scheme for the synthesis of peptide nucleic acid (PNA) is described. First, a resin-bound amino acid is alkylated under Fukuyama-Mitsunobu conditions. A nucleobase is then incorporated via an acid fluoride. Subsequently, oligomerization may be achieved by deprotection, coupling of another amino acid, and repetition of the cycle. Each step of the submonomer synthesis has been optimized to provide essentially quantitative yield.

  DOI：

  10.1021/ol016822y

文献信息

• Optimization of a Solid-Phase Synthesis of a PNA Monomer
  作者：Russell D. Viirre、Robert H. E. Hudson

  DOI：10.1021/ol016822y

  日期：2001.11.1

  [GRAPHICS]A new scheme for the synthesis of peptide nucleic acid (PNA) is described. First, a resin-bound amino acid is alkylated under Fukuyama-Mitsunobu conditions. A nucleobase is then incorporated via an acid fluoride. Subsequently, oligomerization may be achieved by deprotection, coupling of another amino acid, and repetition of the cycle. Each step of the submonomer synthesis has been optimized to provide essentially quantitative yield.