methanediyl-bis-phosphonic acid mono-thymidin-5'-yl ester | 55065-40-2

• 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: methanediyl-bis-phosphonic acid mono-thymidin-5'-yl ester
• 英文别名: [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]methylphosphonic acid
• CAS: 55065-40-2
• 化学式: C₁₁H₁₈N₂O₁₀P₂
• 分子量: 400.219
• InChiKey: ANERRGBVLOSHPI-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3'-O-acetylthymidine 在 水 、 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

文献信息

• Synthesis of 2′-Deoxynucleoside 5′-Methylenebis-(phosphonate)s Using 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate) as the Phosphonylating Agent.
  作者：Krystyna Lesiak、Kyoichi A. Watanabe、Krzysztof W. Pankiewicz

  DOI：10.1080/07328319808004723

  日期：1998.9

  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.