N3-(p-methoxybenzyl)-thymin-1-ylacetic acid | 388606-66-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N3-(p-methoxybenzyl)-thymin-1-ylacetic acid
• 英文别名: N³-PMB-thymin-1-ylacetic acid
• CAS: 388606-66-4
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: WSBQZWYDGBGTGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N3-(p-methoxybenzyl)-thymin-1-ylacetic acid 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到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
• 作为产物：
  描述：

  1-(ethoxycarbonylmethyl)thymine 在 sodium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 N3-(p-methoxybenzyl)-thymin-1-ylacetic 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

文献信息

• A Convenient and Scalable Synthesis of Ethyl <i>N</i>-[(2-Boc-amino)ethyl]glycinate and Its Hydrochloride. Key Intermediates for Peptide Nucleic Acid Synthesis
  作者：Russell D. Viirre、Robert H. E. Hudson

  DOI：10.1021/jo026590w

  日期：2003.2.1

  An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion

  据报道，N-[（2-Boc-氨基）乙基]甘氨酸乙酯及其盐酸盐的合成得到改进。该合成是基于Boc-乙二胺与乙醛酸乙酯水合物的还原烷基化，并且无需色谱即可以接近定量的收率和高纯度提供标题化合物。该化合物原样适合于合成肽核酸单体。此外，转化为盐酸盐提供了稳定的，不吸湿的固体，这是用于处理和储存的方便形式。