2'-deoxy-3-methyl-ψ-uridine | 81691-10-3

• 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: 2'-deoxy-3-methyl-ψ-uridine
• 英文别名: 5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-1H-pyrimidine-2,4-dione
• CAS: 81691-10-3
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: QDIHUJOIPYIRQS-XLPZGREQSA-N

物化性质

• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲基-5-beta-D-呋喃核糖基-2,4(1H,3H)-嘧啶二酮 在 ammonium sulfate 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2'-deoxy-3-methyl-ψ-uridine
  参考文献：
  名称：

  Synthesis of 3-methylpseudouridine and 2′-deoxy-3-methyl-pseudouridine

  摘要：

  The first chemical synthesis of 3-methyl-psi-uridine (5) and its 2'-deoxy analogue (9) has been achieved. psi-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 5 in 82% overall yield. Treatment of 5 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane afforded the 3'5'-protected product, which was converted into the 2'O-[(imidazol-1-yl) thiocarbonyl] derivative 7. Reduction of 7 with tributyltin hydride followed by deblocking of the product gave crystalline 2'-deoxy-3-methyl-psi-uridine (9) in 35% yield form 5.

  DOI：

  10.1016/s0008-6215(00)81043-5

文献信息

• Synthesis of 3-methylpseudouridine and 2′-deoxy-3-methyl-pseudouridine
  作者：Akira Matsuda、Krzysztof Pankiewicz、Bonita K. Marcus、Kyoichi.A. Watanabe、Jack J. Fox

  DOI：10.1016/s0008-6215(00)81043-5

  日期：——

  The first chemical synthesis of 3-methyl-psi-uridine (5) and its 2'-deoxy analogue (9) has been achieved. psi-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 5 in 82% overall yield. Treatment of 5 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane afforded the 3'5'-protected product, which was converted into the 2'O-[(imidazol-1-yl) thiocarbonyl] derivative 7. Reduction of 7 with tributyltin hydride followed by deblocking of the product gave crystalline 2'-deoxy-3-methyl-psi-uridine (9) in 35% yield form 5.