(2R,5R)-9-<2,5-dihydro-5-(phosphonomethoxy)-2-furanyl>adenine ammonium salt | 132178-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2R,5R)-9-<2,5-dihydro-5-(phosphonomethoxy)-2-furanyl>adenine ammonium salt
• 英文别名: ammonium 9-[(2'R,5'R)-2,5-dihydro-5-phosphonomethoxyfuran-2-yl]adenine；[(2R,5R)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]oxymethylphosphonic acid;azane
• CAS: 132178-53-1
• 化学式: C₁₀H₁₂N₅O₅P*H₃N
• 分子量: 330.24
• InChiKey: REQMYJRBFKYHJP-HHQFNNIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,5R)-9-<2,5-dihydro-5-(phosphonomethoxy)-2-furanyl>adenine ammonium salt 在 N,N'-羰基二咪唑 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以40%的产率得到diphosphoryl-(2'R,5'R)-9-(5-phosphonylmethoxy-2,5-dihydrofuran-2-yl)adenine
  参考文献：
  名称：

  Isosteric triphosphonate analogues of dNTP: Synthesis and substrate properties toward various DNA polymerases

  摘要：

  Isosteric triphosphonate derivatives of 2',3'-dideoxy-2',3'-didehydroadenosine and 3'-deoxy-2',3'-didehydrothymidine and their beta,gamma-substituted analogues were synthesized. Their substrate properties toward a number of reverse transcriptases of the human immunodeficiency and avian myeloblastosis viruses, human DNA polymerases alpha and beta, and the Klenow fragment of Escherichia coli DNA polymerase I were studied.

  DOI：

  10.1134/s1068162007050056
• 作为产物：
  描述：

  (2R,4S,5R)-6-N-pivaloyl-9--2-furanyl>adenine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 (2R,5R)-9-<2,5-dihydro-5-(phosphonomethoxy)-2-furanyl>adenine ammonium salt
  参考文献：
  名称：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV

  摘要：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).

  DOI：

  10.1021/jo00008a013

文献信息

• KIM, CHOUNG UN;LUH, BING Y.;MARTIN, JOHN C., J. ORG. CHEM., 56,(1991) N, C. 2642-2647
  作者：KIM, CHOUNG UN、LUH, BING Y.、MARTIN, JOHN C.

  DOI：——

  日期：——