3'-C-methyluridine 2',3'-cyclic monophosphate | 87215-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-C-methyluridine 2',3'-cyclic monophosphate
• 英文别名: 1-(3-C-methyl-β-D-ribofuranosyl)uracil 2',3'-cyclophosphate；1-[(3aR,4R,6R,6aR)-2-hydroxy-4-(hydroxymethyl)-3a-methyl-2-oxo-6,6a-dihydro-4H-furo[3,4-d][1,3,2]dioxaphosphol-6-yl]pyrimidine-2,4-dione
• CAS: 87215-04-1
• 化学式: C₁₀H₁₃N₂O₈P
• 分子量: 320.196
• InChiKey: AHSFTQIHYUDVRQ-AMCGLFBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-C-methyluridine 2',3'-cyclic monophosphate 在 aq. alkali 作用下， 生成 1-(3-C-methyl-β-D-ribofyranosyl)uracil 2'-phosphate 、 1-(3-C-methyl-β-D-ribofyranosyl)uracil 3'-phosphate
  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
• 作为产物：
  描述：

  1-(3-C-methyl-β-D-ribofuranosyl)uracil 生成 3'-C-methyluridine 2',3'-cyclic monophosphate
  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