methyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[(thymine-1-yl)acetyl]glycinate | 172405-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[(thymine-1-yl)acetyl]glycinate
• 英文别名: Methyl 2-(N-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate；methyl 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate
• CAS: 172405-62-8
• 化学式: C₂₇H₂₈N₄O₇
• 分子量: 520.542
• InChiKey: WVTOUZNOPQHNOC-UHFFFAOYSA-N

物化性质

• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139.8
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[(thymine-1-yl)acetyl]glycinate 在 sodium hydroxide 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 作用下， 生成 PNA-胸腺嘧啶单体
  参考文献：
  名称：

  Synthesis of polyamide nucleic acids (PNAs) using a novel Fmoc/Mmt protecting-group combination

  摘要：

  The preparation of 9-Fluorenylmethoxycarbonyl(Fmoc) protected building blocks for the synthesis of polyamide nucleic acids (PNAs) is described. Use of 4-Methoxyphenyldiphenylmethyl (Mmt)-protecting groups for the exocyclic amino function of the nucleobases enhances the solubility of the monomers and allows final deprotection by mild acid treatment. The novel synthetic route is exemplified by the synthesis of heptameric and octameric PNAs.

  DOI：

  10.1016/0960-894x(96)00082-0
• 作为产物：
  描述：

  N-(2-aminoethyl)glycine methyl ester dihydrochloride 在 O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[(thymine-1-yl)acetyl]glycinate
  参考文献：
  名称：

  Synthesis of polyamide nucleic acids (PNAs) using a novel Fmoc/Mmt protecting-group combination

  摘要：

  The preparation of 9-Fluorenylmethoxycarbonyl(Fmoc) protected building blocks for the synthesis of polyamide nucleic acids (PNAs) is described. Use of 4-Methoxyphenyldiphenylmethyl (Mmt)-protecting groups for the exocyclic amino function of the nucleobases enhances the solubility of the monomers and allows final deprotection by mild acid treatment. The novel synthetic route is exemplified by the synthesis of heptameric and octameric PNAs.

  DOI：

  10.1016/0960-894x(96)00082-0

文献信息

• Optimized Synthesis of Fmoc/Boc‐Protected PNA Monomers and their Assembly into PNA Oligomers.
  作者：Ashif Y. Shaikh、Fredrik Björkling、Peter E. Nielsen、Henrik Franzyk

  DOI：10.1002/ejoc.202100278

  日期：2021.5.20

  Fmoc/Boc-protected PNA monomers were efficiently synthesized on a multigram scale and proved compatible with PNA oligomer synthesis by using manual and automated protocols. Screening of coupling conditions included isolation of byproducts and determination of purity by analytical HPLC and MALDI-TOF mass spectrometry; this revealed phosphonium salts as superior coupling reagents for assembly of PNA.

  Fmoc / Boc保护的PNA单体可在数克范围内高效合成，并通过使用手动和自动方案证明与PNA低聚物合成兼容。偶联条件的筛选包括副产物的分离以及通过分析型HPLC和MALDI-TOF质谱测定纯度；这表明phospho盐是组装PNA的优良偶联剂。