1-<<(3S),4-dihydroxy-1-phosphonyl-(2R)-butoxy>methyl>thymine

• 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: 1-<<(3S),4-dihydroxy-1-phosphonyl-(2R)-butoxy>methyl>thymine
• 英文别名: [(2S,3S)-3,4-dihydroxy-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]butyl]phosphonic acid
• 化学式: C₁₀H₁₇N₂O₈P
• 分子量: 324.227
• InChiKey: AKTOMHJHOYJVRE-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphoryl-2-phenylmethoxybutoxy]methylbenzene 在 palladium dihydroxide 、 三甲基溴硅烷 、 四乙基碘化铵 作用下， 以 乙醇 、 二氯甲烷 、 环己烯 为溶剂， 反应 40.0h， 生成 1-<<(3S),4-dihydroxy-1-phosphonyl-(2R)-butoxy>methyl>thymine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1‘,2‘-Seconucleo-5‘-phosphonates

  摘要：

  A series of 1',2'-seconucleophosphonate analogues were prepared containing adenine, cytosine, thymine, and uracil as the nucleobase. The synthetic methodology is efficient and uses chloromethyl ethers derived from the chirons diethyl (3S)-(benzyloxy)-(2R)-hydroxybutanephosphonate (1) and diethyl (3S),4-bis(benzyloxy)-(2R)-hydroxybutanephosphonate (2). Selected deblocked derivatives, i.e., two monoesters (13 and 14), four phosphonic acids (15-18), and one cyclic phosphonate (23), were screened for in vitro activity against certain RNA, adeno, and HIV viruses. All of them were found to be devoid of activity.

  DOI：

  10.1021/jm9506783

文献信息

• Synthesis and Biological Evaluation of 1‘,2‘-Seconucleo-5‘-phosphonates
  作者：Saibaba Racha、Chandra Vargeese、Purushotham Vemishetti、Hussein I. El-Subbagh、Elie Abushanab、Raymond P. Panzica

  DOI：10.1021/jm9506783

  日期：1996.1.1

  A series of 1',2'-seconucleophosphonate analogues were prepared containing adenine, cytosine, thymine, and uracil as the nucleobase. The synthetic methodology is efficient and uses chloromethyl ethers derived from the chirons diethyl (3S)-(benzyloxy)-(2R)-hydroxybutanephosphonate (1) and diethyl (3S),4-bis(benzyloxy)-(2R)-hydroxybutanephosphonate (2). Selected deblocked derivatives, i.e., two monoesters (13 and 14), four phosphonic acids (15-18), and one cyclic phosphonate (23), were screened for in vitro activity against certain RNA, adeno, and HIV viruses. All of them were found to be devoid of activity.