[(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphorylbutan-2-yl]oxymethylbenzene | 1027564-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphorylbutan-2-yl]oxymethylbenzene
• CAS: 1027564-02-8
• 化学式: C₁₆H₂₆ClO₅P
• 分子量: 364.806
• InChiKey: WIOKQVFROGMWRY-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphorylbutan-2-yl]oxymethylbenzene 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)-hydroxy-1-phosphonyl-(2R)-butoxy>methyl>uracil
  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
• 作为产物：
  描述：

  聚合甲醛 、 Diethyl (2R,3S)-3-(benzyloxy)-2-hydroxybutanephosphonate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 [(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphorylbutan-2-yl]oxymethylbenzene
  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.