1-((2R,3S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-hydroxy-5-methyl-tetrahydro-furan-2-yl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione | 223378-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,3S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-hydroxy-5-methyl-tetrahydro-furan-2-yl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione
• CAS: 223378-21-0
• 化学式: C₂₆H₂₇BrN₂O₆
• 分子量: 543.414
• InChiKey: GLUWBWVADSFBGL-NPLBNZISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-hydroxy-5-methyl-tetrahydro-furan-2-yl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到5-[(E)-2-bromoethenyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-5-methyloxolan-2-yl]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：

  在 吡啶 、 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 1-((2R,3S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-hydroxy-5-methyl-tetrahydro-furan-2-yl)-5-((E)-2-bromo-vinyl)-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