6-(dihydroxymethyl)-2',3',5'-tris-O-(methoxymethyl)uridine-hydrate-13C | 138386-02-4

• 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: 6-(dihydroxymethyl)-2',3',5'-tris-O-(methoxymethyl)uridine-hydrate-13C
• CAS: 138386-02-4
• 化学式: C₁₆H₂₆N₂O₁₁
• 分子量: 423.378
• InChiKey: NXJPQOKOJPLTMD-RMRIROOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  159.93
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  尿嘧啶核苷 在 三氟甲磺酸 水 、 lithium diisopropyl amide 作用下， 以 氘代二甲亚砜 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 6-(dihydroxymethyl)-2',3',5'-tris-O-(methoxymethyl)uridine-hydrate-13C
  参考文献：
  名称：

  Facile addition of hydroxylic nucleophiles to the formyl group of uridine-6-carboxaldehydes

  摘要：

  The ''instability'' previously ascribed to the tri-O-protected 6-formyluridines has been shown to be due to a facile hydration of the aldehyde functionality. Using an efficient protecting group strategy, 2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde (2) was prepared in two steps from uridine. Aldehyde 2 was shown to undergo a reversible hydration reaction in (CD3)2SO solution to give the gem-diol 3, according to extensive H-1 and C-13 1D and 2D NMR spectroscopic analyses. This gem-diol was the sole structure detected in D2O solution. The diethyl acetal derivative 4 provided spectral data for comparison to that of 3. Compound 2 afforded diastereomeric hemiacetal products upon treatment with alcohols, and deprotection of 2 afforded the heretofore unknown uridine-6-carboxaldehyde, which was found to exist as a 1:10 mixture of free aldehyde A and a 5'-cyclic hemiacetal structure D in dry (CD3)2SO solution, but as a 1:2 mixture of a 5'-cyclic hemiacetal structure D and the gem-diol B in D2O solution, by NMR.

  DOI：

  10.1021/jo00029a027