Phosphoric acid mono-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-4-methyl-tetrahydro-furan-3-yl] ester | 141635-72-5

• 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
• 英文名称: Phosphoric acid mono-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-4-methyl-tetrahydro-furan-3-yl] ester
• 英文别名: [(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] dihydrogen phosphate
• CAS: 141635-72-5
• 化学式: C₁₀H₁₅N₂O₉P
• 分子量: 338.211
• InChiKey: LIUHDVSVOFIGDF-VPCXQMTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2'-C-methyluridine 2',3'-cyclic monophosphate 在 aq. alkali 作用下， 生成 Phosphoric acid mono-[(2R,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-3-methyl-tetrahydro-furan-3-yl] ester 、 Phosphoric acid mono-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-4-methyl-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  Hydrolysis of 2'- and 3'-C-methyluridine 2',3'-cyclic monophosphates and interconversion and dephosphorylation of the resulting 2'- and 3'-monophosphates: comparison with the reactions of uridine monophosphates.

  摘要：

  2',3'-Cyclic monophosphates of 2'- and 3'-C-methyluridines have been prepared and shown to hydrolyze to a mixture of the corresponding 2'- and 3'-monophosphates. The predominant product isomer is the one having the tertiary hydroxyl group phosphorylated, but on longer treatment a phosphate migration from the tertiary to secondary hydroxyl function takes place. Hydrolytic dephosphorylation competes with the phosphate migration, the tertiary hydroxyl group being dephosphorylated 1 order of magnitude faster than the secondary one. Kinetics of the partial reactions have been described and compared to the data obtained with uridine 2',3'-cyclic monophosphate. The tertiary monophosphate has been shown to be exceptionally susceptible to nucleophilic attack of the neighboring hydroxyl group.

  DOI：

  10.1021/jo00041a014