[(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[hydroxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]methyl]phosphinic acid | 203121-58-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[hydroxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]methyl]phosphinic acid
• CAS: 203121-58-8
• 化学式: C₂₁H₂₇N₃O₁₃P₂
• 分子量: 591.405
• InChiKey: JIPBSFDLTDLRQQ-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  224
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[hydroxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]methyl]phosphinic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 methanediyl-bis-phosphonic acid mono-thymidin-5'-yl ester
  参考文献：
  名称：

  Synthesis of 2′-Deoxynucleoside 5′-Methylenebis-(phosphonate)s Using 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate) as the Phosphonylating Agent.

  摘要：

  2-(4-Nitrophenylethyl) methylenebis(phosphonate) (1) has been prepared by reaction of 2-(4-nitrophenyl)ethyl alcohol with methylenebis(phosphonyl) tetrachloride. Compound 1 was treated with diisopropylcarbodiimide (DIC) to give bicyclic intermediate 2, which in reaction with suitably protected 2'-deoxynucleosides 3 gave P-1,P-2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by beta-elimination with DBU afforded the corresponding 2'-deoxynucleoside 5'-methylene-bis(phosphonate) analogues 5.

  DOI：

  10.1080/07328319808004723
• 作为产物：
  描述：

  3'-O-acetyl-2'-deoxy-5'-O-(dimethoxytrityl)thymidine 在 水 、 溶剂黄146 作用下， 生成 [(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[hydroxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]methyl]phosphinic acid
  参考文献：
  名称：

  Synthesis of 2′-Deoxynucleoside 5′-Methylenebis-(phosphonate)s Using 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate) as the Phosphonylating Agent.

  摘要：

  2-(4-Nitrophenylethyl) methylenebis(phosphonate) (1) has been prepared by reaction of 2-(4-nitrophenyl)ethyl alcohol with methylenebis(phosphonyl) tetrachloride. Compound 1 was treated with diisopropylcarbodiimide (DIC) to give bicyclic intermediate 2, which in reaction with suitably protected 2'-deoxynucleosides 3 gave P-1,P-2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by beta-elimination with DBU afforded the corresponding 2'-deoxynucleoside 5'-methylene-bis(phosphonate) analogues 5.

  DOI：

  10.1080/07328319808004723