3',5'-di-O-acetyl-2'-bromo-2'-deoxy-5-acetoxymethyl-uridine | 210469-36-6

• 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: 3',5'-di-O-acetyl-2'-bromo-2'-deoxy-5-acetoxymethyl-uridine
• 英文别名: [(2R,3R,4R,5R)-3-acetyloxy-5-[5-(acetyloxymethyl)-2,4-dioxopyrimidin-1-yl]-4-bromooxolan-2-yl]methyl acetate
• CAS: 210469-36-6
• 化学式: C₁₆H₁₉BrN₂O₉
• 分子量: 463.239
• InChiKey: LPGCRDWMRGDMFM-RGCMKSIDSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-2'-bromo-2'-deoxy-5-acetoxymethyl-uridine 在 三甲基氯硅烷 、 氨 、 二甲基亚砜 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 28.1h， 生成 5-Chloromethyl-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms

  摘要：

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

  DOI：

  10.1080/15257770008033040
• 作为产物：
  描述：

  乙酰溴 、 5-羟甲基尿苷 以 乙腈 为溶剂， 反应 0.5h， 以44%的产率得到3',5'-di-O-acetyl-2'-bromo-2'-deoxy-5-acetoxymethyl-uridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms

  摘要：

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

  DOI：

  10.1080/15257770008033040