1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione | 81691-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione
• CAS: 81691-05-6
• 化学式: C₂₁H₄₀N₂O₇Si₃
• 分子量: 516.814
• InChiKey: QEKYONFPTOVZNH-HCXYKTFWSA-N

物化性质

• 沸点：
  485.0±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  97.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione 在 氨 作用下， 生成 3-甲基-5-beta-D-呋喃核糖基-2,4(1H,3H)-嘧啶二酮
  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
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 1-acetyl-2',3',5'-tri-O-trimethylsilyl-ψ-uridine 以 苯 为溶剂， 反应 1.0h， 生成 1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione
  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