5-methyl-1-((1R,3R,4S)-3-(((8-methyl-2-oxido-4H-benzo[d][1,3,2]dioxaphosphinin-2-yl)oxy)methyl)-4-thiocyanatocyclopentyl)pyrimidine-2,4(1H,3H)-dione | 908240-46-0

• 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: 5-methyl-1-((1R,3R,4S)-3-(((8-methyl-2-oxido-4H-benzo[d][1,3,2]dioxaphosphinin-2-yl)oxy)methyl)-4-thiocyanatocyclopentyl)pyrimidine-2,4(1H,3H)-dione
• CAS: 908240-46-0
• 化学式: C₂₀H₂₂N₃O₆PS
• 分子量: 463.451
• InChiKey: OGFGPPWZQFNKRH-JRTFIDCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123.41
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-methyl-1-((1R,3R,4S)-3-(((8-methyl-2-oxido-4H-benzo[d][1,3,2]dioxaphosphinin-2-yl)oxy)methyl)-4-thiocyanatocyclopentyl)pyrimidine-2,4(1H,3H)-dione 在 水 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 carba-3'-thiocyanato-2'-deoxythymidine monophosphate
  参考文献：
  名称：

  SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE

  摘要：

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.

  DOI：

  10.1081/ncn-200060251
• 作为产物：
  描述：

  3-methylsalicylchlorophosphane 在 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 5-methyl-1-((1R,3R,4S)-3-(((8-methyl-2-oxido-4H-benzo[d][1,3,2]dioxaphosphinin-2-yl)oxy)methyl)-4-thiocyanatocyclopentyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE

  摘要：

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.

  DOI：

  10.1081/ncn-200060251