(2R,3R,4S,5R)-2-[4-(4-aminopyrimidin-5-yl)imidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol | 832730-77-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: (2R,3R,4S,5R)-2-[4-(4-aminopyrimidin-5-yl)imidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 832730-77-5
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: BXOKKXWAUYYDQM-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-2-[4-(4-aminopyrimidin-5-yl)imidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol 在 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以68%的产率得到5-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]-1H-pyrimidin-6-one
  参考文献：
  名称：

  “Molecular Chameleons”. Design and Synthesis of C-4-Substituted Imidazole Fleximers

  摘要：

  The synthesis of two flexible nucleosides is presented. The "fleximers" feature the purine ring system split into its imidazole and pyrimidine components. This modification serves to introduce flexibility to the nucleoside while still retaining the elements essential for molecular recognition. As a result, these structurally innovative nucleosides can more readily adapt to capricious binding sites and, as such, should find use for investigating enzyme-coenzyme as well as nucleic acid-protein interactions.

  DOI：

  10.1021/ol047895v
• 作为产物：
  描述：

  4(5)-腈甲基咪唑 在 sodium methylate 、 牛血清白蛋白 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 39.0h， 生成 (2R,3R,4S,5R)-2-[4-(4-aminopyrimidin-5-yl)imidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  “Molecular Chameleons”. Design and Synthesis of C-4-Substituted Imidazole Fleximers

  摘要：

  The synthesis of two flexible nucleosides is presented. The "fleximers" feature the purine ring system split into its imidazole and pyrimidine components. This modification serves to introduce flexibility to the nucleoside while still retaining the elements essential for molecular recognition. As a result, these structurally innovative nucleosides can more readily adapt to capricious binding sites and, as such, should find use for investigating enzyme-coenzyme as well as nucleic acid-protein interactions.

  DOI：

  10.1021/ol047895v

文献信息

• “Molecular Chameleons”. Design and Synthesis of C-4-Substituted Imidazole Fleximers
  作者：Katherine L. Seley、Samer Salim、Liang Zhang

  DOI：10.1021/ol047895v

  日期：2005.1.1

  The synthesis of two flexible nucleosides is presented. The "fleximers" feature the purine ring system split into its imidazole and pyrimidine components. This modification serves to introduce flexibility to the nucleoside while still retaining the elements essential for molecular recognition. As a result, these structurally innovative nucleosides can more readily adapt to capricious binding sites and, as such, should find use for investigating enzyme-coenzyme as well as nucleic acid-protein interactions.