4-(2S)-[2-(diisopropoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(diisopropoxyphosphorylmethoxy)propoxy]-2-(methylsulfonyl)pyrimidine | 1160513-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-(2S)-[2-(diisopropoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(diisopropoxyphosphorylmethoxy)propoxy]-2-(methylsulfonyl)pyrimidine
• 英文别名: (2S)-2-[di(propan-2-yloxy)phosphorylmethoxy]-3-[6-[(2S)-2-[di(propan-2-yloxy)phosphorylmethoxy]propoxy]-2-methylsulfonylpyrimidin-4-yl]oxypropan-1-ol
• CAS: 1160513-08-5
• 化学式: C₂₅H₄₈N₂O₁₃P₂S
• 分子量: 678.675
• InChiKey: STAFGDYCKYKSHL-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-(2S)-[2-(diisopropoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(diisopropoxyphosphorylmethoxy)propoxy]-2-(methylsulfonyl)pyrimidine 在 氨 作用下， 以 四氢呋喃 为溶剂， 生成 (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
  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
• 作为产物：
  描述：

  (2S)-2-[di(propan-2-yloxy)phosphorylmethoxy]-3-[6-[(2S)-2-[di(propan-2-yloxy)phosphorylmethoxy]propoxy]-2-methylsulfanylpyrimidin-4-yl]oxypropan-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以18%的产率得到4-(2S)-[2-(diisopropoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-(2S)-[2-(diisopropoxyphosphorylmethoxy)propoxy]-2-(methylsulfonyl)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