(2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-(ethanoyloxy)ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate | 1104733-87-0

• 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: (2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-(ethanoyloxy)ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
• CAS: 1104733-87-0
• 化学式: C₂₅H₂₉N₃O₁₁
• 分子量: 547.519
• InChiKey: FAMVDCLUHGQBDQ-JSSYZSAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  181.32
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-(ethanoyloxy)ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  De Novo Synthetic Route to a Combinatorial Library of Peptidyl Nucleosides

  摘要：

  A stereoselective synthetic route has been developed for the combinatorial synthesis of a structurally unique class of C-4' side chain modified peptide-linked nucleosides. The synthetic strategy and approach involves initial synthesis of a strategically functionalized amino butenolide template, utilizing L-serine as a chiral starting material. Subsequent transformation of the above lactone to C4' aminoalkyl substituted nucleosides, followed by the peptidic coupling of the C4' side chain amine with various amino acids completed the syntheses of the target peptidyl nucleosides. Employing the above route, and utilizing a combination of easily available nucleobases (4) and amino acids (6) as the two diversity elements, synthesis of a 24-member combinatorial library of the title peptide-linked nucleosides has been accomplished.

  DOI：

  10.1080/15257770801944394
• 作为产物：
  描述：

  (2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-hydroxyethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以183 mg的产率得到(2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-(ethanoyloxy)ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
  参考文献：
  名称：

  De Novo Synthetic Route to a Combinatorial Library of Peptidyl Nucleosides

  摘要：

  A stereoselective synthetic route has been developed for the combinatorial synthesis of a structurally unique class of C-4' side chain modified peptide-linked nucleosides. The synthetic strategy and approach involves initial synthesis of a strategically functionalized amino butenolide template, utilizing L-serine as a chiral starting material. Subsequent transformation of the above lactone to C4' aminoalkyl substituted nucleosides, followed by the peptidic coupling of the C4' side chain amine with various amino acids completed the syntheses of the target peptidyl nucleosides. Employing the above route, and utilizing a combination of easily available nucleobases (4) and amino acids (6) as the two diversity elements, synthesis of a 24-member combinatorial library of the title peptide-linked nucleosides has been accomplished.

  DOI：

  10.1080/15257770801944394