2-amino-4-(2S)-[2-(phosphonomethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(phosphonomethoxy)propoxy]pyrimidine | 1160513-20-1

• 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: 2-amino-4-(2S)-[2-(phosphonomethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(phosphonomethoxy)propoxy]pyrimidine
• 英文别名: [(2S)-1-[2-amino-6-[(2S)-3-hydroxy-2-(phosphonomethoxy)propoxy]pyrimidin-4-yl]oxypropan-2-yl]oxymethylphosphonic acid
• CAS: 1160513-20-1
• 化学式: C₁₂H₂₃N₃O₁₁P₂
• 分子量: 447.276
• InChiKey: DZFSSEHTXXELJK-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (2S)-3-[2-amino-6-[(2S)-2-[di(propan-2-yloxy)phosphorylmethoxy]propoxy]pyrimidin-4-yl]oxy-2-[di(propan-2-yloxy)phosphorylmethoxy]propan-1-ol 在 三甲基溴硅烷 、 水 作用下， 以 乙腈 为溶剂， 以67%的产率得到2-amino-4-(2S)-[2-(phosphonomethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(phosphonomethoxy)propoxy]pyrimidine
  参考文献：
  名称：

  Acyclic nucleoside bisphosphonates: Synthesis and properties of chiral 2-amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines

  摘要：

  2-Amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines bearing two equal or different achiral or chiral phosphonoalkoxy chains have been prepared either by aromatic nucleophilic substitution of 2-amino-4,6-dichloropyrimidine or by alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine with appropriate phosphonate-bearing building block. Alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine proved to be the method of choice for efficient preparation of variety of bisphosphonates. The enantiomeric purity of selected compounds was determined by capillary electrophoresis. Antiviral activity of bisphosphonates is discussed. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.031