(2R,5R)-1-<2,5-dihydro-5-<(dimethoxyphosphinyl)methoxy>-2-furanyl>thymine | 132178-48-4

• 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: (2R,5R)-1-<2,5-dihydro-5-<(dimethoxyphosphinyl)methoxy>-2-furanyl>thymine
• 英文别名: 1-[(2R,5R)-5-(dimethoxyphosphorylmethoxy)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 132178-48-4
• 化学式: C₁₂H₁₇N₂O₇P
• 分子量: 332.25
• InChiKey: OSXIQTQMSKWLOZ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-<2,5-dihydro-5-<(dimethoxyphosphinyl)methoxy>-2-furanyl>thymine 在 三甲基溴硅烷 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2'R,5'R)-1-(5-phosphonylmethoxy-2,5-dihydrofuran-2-yl)thymine
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038
• 作为产物：
  描述：

  (2'R)-1-(2,3-dihydrofuran-2-yl)thymine 在 sodium periodate 、 silver perchlorate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.8h， 生成 (2R,5R)-1-<2,5-dihydro-5-<(dimethoxyphosphinyl)methoxy>-2-furanyl>thymine
  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：——