1-(2-acetylamino-β-D-2-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione | 96196-54-2

• 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: 1-(2-acetylamino-β-D-2-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-(2,4-dioxopyrimidin-1-yl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 96196-54-2
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: PIJBBOVZQVIFDP-NENRSDFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  148
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-acetylamino-β-D-2-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione 在 sodium azide 、 一氯化碘 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 以50%的产率得到N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis and Reactions of Some Uracil and 5-Halouracil Nucleosides of 2-Acetamido-2-deoxy-D-glucose.

  摘要：

  Silylated uracils react with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucose (5) under trimethylsilyl trifluoromethanesulfonate catalysis to give the nucleosides 6, 8, 10 and 12, respectively, as well as the diglycoside 14. Deblocking with sodium methoxide in methanol afforded the free nucleosides 7, 9, 11 and 13, respectively. Alternatively, the free nucleosides 11 and 13 were obtained directly by halogenation of 7 with N-bromosuccinimide or iodine monochloride, respectively. The structures of the synthesized compounds were confirmed by their H-1 NMR, UV and mass spectra and elemental analyses.

  DOI：

  10.3891/acta.chem.scand.51-0958
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(2,4-dioxopyrimidin-1-yl)oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以78%的产率得到1-(2-acetylamino-β-D-2-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Reactions of Some Uracil and 5-Halouracil Nucleosides of 2-Acetamido-2-deoxy-D-glucose.

  摘要：

  Silylated uracils react with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucose (5) under trimethylsilyl trifluoromethanesulfonate catalysis to give the nucleosides 6, 8, 10 and 12, respectively, as well as the diglycoside 14. Deblocking with sodium methoxide in methanol afforded the free nucleosides 7, 9, 11 and 13, respectively. Alternatively, the free nucleosides 11 and 13 were obtained directly by halogenation of 7 with N-bromosuccinimide or iodine monochloride, respectively. The structures of the synthesized compounds were confirmed by their H-1 NMR, UV and mass spectra and elemental analyses.

  DOI：

  10.3891/acta.chem.scand.51-0958