2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde | 138385-99-6

• 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: 2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde
• 英文别名: 3-[(2R,3R,4R,5R)-3,4-bis(methoxymethoxy)-5-(methoxymethoxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carbaldehyde
• CAS: 138385-99-6
• 化学式: C₁₆H₂₄N₂O₁₀
• 分子量: 404.374
• InChiKey: QGHSYJHJUXMFSZ-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde 在 重水 作用下， 以 氘代二甲亚砜 为溶剂， 生成
  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
• 作为产物：
  描述：

  尿嘧啶核苷 在 三氟甲磺酸 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde
  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

文献信息

• Facile addition of hydroxylic nucleophiles to the formyl group of uridine-6-carboxaldehydes
  作者：Michael P. Groziak、Ali Koohang

  DOI：10.1021/jo00029a027

  日期：1992.1

  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.