6-amino-4-(ethoxycarbonyl)-5-methyl-2-(((p-tolylsulfonyl)oxy)methyl)pyrimidine | 142582-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-4-(ethoxycarbonyl)-5-methyl-2-(((p-tolylsulfonyl)oxy)methyl)pyrimidine
• 英文别名: Ethyl 6-amino-5-methyl-2-[(4-methylphenyl)sulfonyloxymethyl]pyrimidine-4-carboxylate
• CAS: 142582-31-8
• 化学式: C₁₆H₁₉N₃O₅S
• 分子量: 365.41
• InChiKey: SFVFOMWGYGQJTE-UHFFFAOYSA-N

物化性质

• 沸点：
  549.6±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-amino-4-(ethoxycarbonyl)-5-methyl-2-(((p-tolylsulfonyl)oxy)methyl)pyrimidine 在 lithium hydroxide 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 45.0h， 生成 N^α,N^β-bis(tert-butoxycarbonyl)-N^β-<(4-amino-6-carboxy-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanineamide
  参考文献：
  名称：

  Synthesis of desacetamidopyrimidoblamic acid and deglyco desacetamidobleomycin A2

  摘要：

  A concise synthesis of desacetamidopyrimidoblamic acid (3) is detailed based on the inverse electron demand [4 + 2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine (5) with 1-bis(benzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The incorporation of 3 into synthetic deglyco desacetamidobleomycin A2 (4) and the pr comparison of the functional cleavage of duplex DNA by Fe(II)-4 are described. Fe(II)-4 proved to be 0.3-0.2x as effective as Fe(II)-deglycobleomycin A2 in its efficiency of cleavage of supercoiled phi-X174 RFI DNA.

  DOI：

  10.1021/jo00042a004
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三甲酸三乙酯 在 sodium tetrahydroborate 、 三氟甲磺酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 6-amino-4-(ethoxycarbonyl)-5-methyl-2-(((p-tolylsulfonyl)oxy)methyl)pyrimidine
  参考文献：
  名称：

  Total Synthesis of Bleomycin A2 and Related Agents. 2. Synthesis of (-)-Pyrimidoblamic Acid, epi-(+)-Pyrimidoblamic Acid, (+)-Desacetamidopyrimidoblamic Acid, and (-)-Descarboxamidopyrimidoblamic Acid

  摘要：

  Full details of concise syntheses of (-)-pyrimidoblamic acid (1), the authentic heterocyclic core of the bleomycin A(2) metal binding domain, as well as the key substructure analogs epi-(+)-pyrimidoblamic acid (2), (+)-desacetamidopyrimidoblamic acid (3), and (-)-descarboxamidppyrimidoblamic acid (4) are described. Key to the approach is the implementation of an inverse electron demand [4 + 2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine with 1-(dibenzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The development and subsequent implementation of a diastereoselective imine addition reaction of optically active N-acyloxazolidinone enolates provided a stereocontrolled introduction of the pyrimidoblamic acid C2 acetamido side chain. Chemical studies which unambiguously establish and confirm the absolute configuration of the C2 acetamido side chain are detailed, and their extension to the synthesis of (-)-descarboxamidopyrimidoblamic acid (4) is described.

  DOI：

  10.1021/ja00092a012

文献信息

• Synthesis of desacetamidopyrimidoblamic acid and deglyco desacetamidobleomycin A2
  作者：Dale L. Boger、Royce F. Menezes、Qun Dang

  DOI：10.1021/jo00042a004

  日期：1992.7

  A concise synthesis of desacetamidopyrimidoblamic acid (3) is detailed based on the inverse electron demand [4 + 2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine (5) with 1-bis(benzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The incorporation of 3 into synthetic deglyco desacetamidobleomycin A2 (4) and the pr comparison of the functional cleavage of duplex DNA by Fe(II)-4 are described. Fe(II)-4 proved to be 0.3-0.2x as effective as Fe(II)-deglycobleomycin A2 in its efficiency of cleavage of supercoiled phi-X174 RFI DNA.
• Total Synthesis of Bleomycin A2 and Related Agents. 2. Synthesis of (-)-Pyrimidoblamic Acid, epi-(+)-Pyrimidoblamic Acid, (+)-Desacetamidopyrimidoblamic Acid, and (-)-Descarboxamidopyrimidoblamic Acid
  作者：Dale L. Boger、Takeshi Honda、Qun Dang

  DOI：10.1021/ja00092a012

  日期：1994.6

  Full details of concise syntheses of (-)-pyrimidoblamic acid (1), the authentic heterocyclic core of the bleomycin A(2) metal binding domain, as well as the key substructure analogs epi-(+)-pyrimidoblamic acid (2), (+)-desacetamidopyrimidoblamic acid (3), and (-)-descarboxamidppyrimidoblamic acid (4) are described. Key to the approach is the implementation of an inverse electron demand [4 + 2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine with 1-(dibenzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The development and subsequent implementation of a diastereoselective imine addition reaction of optically active N-acyloxazolidinone enolates provided a stereocontrolled introduction of the pyrimidoblamic acid C2 acetamido side chain. Chemical studies which unambiguously establish and confirm the absolute configuration of the C2 acetamido side chain are detailed, and their extension to the synthesis of (-)-descarboxamidopyrimidoblamic acid (4) is described.

表征谱图