(E)-3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid | 223378-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (E)-3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid
• CAS: 223378-19-6
• 化学式: C₁₃H₁₆N₂O₇
• 分子量: 312.279
• InChiKey: MRMKACKVBWVVSN-HCTDIBLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  141.85
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到5-((E)-2-Bromo-vinyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of novel 4′-C-methyl-pyrimidine nucleosides and their biological activities

  摘要：

  Two novel 4'-C-methylnucleosides, 4'-methylBVDU 9 and 4'-methylBVaraU 10, were synthesized. The farmer was derived from 3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine 12, and the latter was produced via glycosylation between 4-C-methyl-D-ribose derivative 11 and a silylated bromovinyl uracil. 4'-MethylBVDU 9 exhibited particularly potent anti-varicella-zoster virus (VZV) activity in vitro. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00090-6
• 作为产物：
  描述：

  3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine 在 palladium diacetate 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 生成 (E)-3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid
  参考文献：
  名称：

  Synthesis of novel 4′-C-methyl-pyrimidine nucleosides and their biological activities

  摘要：

  Two novel 4'-C-methylnucleosides, 4'-methylBVDU 9 and 4'-methylBVaraU 10, were synthesized. The farmer was derived from 3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine 12, and the latter was produced via glycosylation between 4-C-methyl-D-ribose derivative 11 and a silylated bromovinyl uracil. 4'-MethylBVDU 9 exhibited particularly potent anti-varicella-zoster virus (VZV) activity in vitro. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00090-6