拉米夫定单磷酸铵盐 | 1187058-40-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 拉米夫定单磷酸铵盐
• 中文别名: 拉米夫定单磷酸酯铵盐
• 英文名称: 1-(2',3'-dideoxy-3'-thia-β-L-ribofuranosyl)-cytosine-5'-monophosphate, ammonium salt
• 英文别名: Ammonium [(2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl]methyl hydrogen phosphate；azanium;[(2R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl hydrogen phosphate
• CAS: 1187058-40-7
• 化学式: C₈H₁₂N₃O₆PS*H₃N
• 分子量: 326.27
• InChiKey: QVKKAWUJZGRQKI-UOERWJHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 反应 1.0h， 以64%的产率得到拉米夫定单磷酸铵盐
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxynucleoside Phosphoesters Using H-Phosphonate Chemistry on Soluble Polymer Support

  摘要：

  Phosphorylation of ddC and 3TC was efficiently performed on soluble poly(ethylene glycol) support. The corresponding 5'-monophosphate derivatives were obtained by oxidation of the support bound 5'-H-phosphonate intermediates. Then, di- and triphosphorylations were carried out using a carbonyldiimidazole activation step followed by nucleophilic substitution with suitable phosphate salts. Trivalent phosphorus chemistry appeared as a good alternative for monophosphate synthesis of acid-sensitive 2',3'-dideoxynucleosides.

  DOI：

  10.1021/jo1022958