(5-Cyclohexyl-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane | 1027429-95-3

• 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: (5-Cyclohexyl-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane
• CAS: 1027429-95-3
• 化学式: C₁₆H₃₀N₂O₂Si₂
• 分子量: 338.597
• InChiKey: ZAPOFTWPPVVSPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-Cyclohexyl-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 5-cyclohexyl-2"-deoxyuridine
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234
• 作为产物：
  描述：

  环己基乙酸甲酯 在 氯乙酸 、 六甲基二硅氮烷 、 lithium diisopropyl amide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (5-Cyclohexyl-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234

文献信息

• The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines
  作者：I. Basnak、A. Balkan、P. L. Coe、R. T. Walker

  DOI：10.1080/15257779408013234

  日期：1994.3

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.