[(2R,3S,5R)-3-acetyloxy-5-[2-oxo-4-(tetrazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate | 175601-12-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-3-acetyloxy-5-[2-oxo-4-(tetrazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 175601-12-4
• 化学式: C₁₄H₁₆N₆O₆
• 分子量: 364.318
• InChiKey: JDTZBBAXQUQAEJ-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[2-oxo-4-(tetrazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 吡啶 、 邻苯二甲酸亚胺 、 水 、 三乙胺 作用下， 生成 3',5'-di-O-acetyl-2'-deoxycytidine
  参考文献：
  名称：

  An Efficient Method for the Synthesis of [4–¹⁵N]Cytidine, 2′-Deoxy[4–¹⁵N]Cytidine, [6–¹⁵N]adenosine, and 2′-Deoxy [6–¹⁵N]adenosine Derivatives

  摘要：

  Nucleophilic substitution reactions of 4-azolyl-1-beta-D-ribofuranosyl-pyrimidin-2(1H)-one and 6-azolyl-9-beta-D-ribofuranosyl-9H-purine derivatives, which were converted from uridine and inosine, with [N-15]phthalimide in the presence of triethylamine or DBU gave N-4-phthaloyl[4-N-15]cytidine and N-6-phthaloyl[6-N-15]- adenosine derivatives, respectively, in high yields. Similar reactions of those azolyl derivatives with succinimide afforded N-4-succinylcytidine and N-6-succinyladenosine derivatives in high yields. The corresponding 2'-deoxyribonucleosides were also synthesized efficiently through the same procedure.

  DOI：

  10.1080/07328319608002421
• 作为产物：
  描述：

  2-脱氧尿苷 在 磷酸二苯酯 、 对甲苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 [(2R,3S,5R)-3-acetyloxy-5-[2-oxo-4-(tetrazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  An Efficient Method for the Synthesis of [4–¹⁵N]Cytidine, 2′-Deoxy[4–¹⁵N]Cytidine, [6–¹⁵N]adenosine, and 2′-Deoxy [6–¹⁵N]adenosine Derivatives

  摘要：

  Nucleophilic substitution reactions of 4-azolyl-1-beta-D-ribofuranosyl-pyrimidin-2(1H)-one and 6-azolyl-9-beta-D-ribofuranosyl-9H-purine derivatives, which were converted from uridine and inosine, with [N-15]phthalimide in the presence of triethylamine or DBU gave N-4-phthaloyl[4-N-15]cytidine and N-6-phthaloyl[6-N-15]- adenosine derivatives, respectively, in high yields. Similar reactions of those azolyl derivatives with succinimide afforded N-4-succinylcytidine and N-6-succinyladenosine derivatives in high yields. The corresponding 2'-deoxyribonucleosides were also synthesized efficiently through the same procedure.

  DOI：

  10.1080/07328319608002421