5-叔丁基-2'-脱氧尿苷 | 60136-06-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-叔丁基-2'-脱氧尿苷
• 英文名称: 5-tert-Butyl-2'-deoxyuridine
• 英文别名: 5-tert-butyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione；5-tert-butyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 60136-06-3
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: HVRGZMYYSQCLQS-IVZWLZJFSA-N

物化性质

• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-叔丁基-2'-脱氧尿苷 在 水 作用下， 以 水 为溶剂， 反应 49.5h， 生成 6-hydroxy-5,6-dihydro-2'-deoxy-uridine
  参考文献：
  名称：

  Basnak, Ivan; McKinnell, Denise; Spencer, Neil, Journal of the Chemical Society. Perkin transactions I, 1997, # 2, p. 121 - 125

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 5-叔丁基-2'-脱氧尿苷
  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

• Basnak, I.; McKinnell, D.; Spencer, N., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S5 - S8
  作者：Basnak, I.、McKinnell, D.、Spencer, N.、Ashton, P. R.、Hamor, T. A.、Walker, R. T.

  DOI：——

  日期：——
• Basnak, Ivan; McKinnell, Denise; Spencer, Neil, Journal of the Chemical Society. Perkin transactions I, 1997, # 2, p. 121 - 125
  作者：Basnak, Ivan、McKinnell, Denise、Spencer, Neil、Balkan, Ayla、Ashton, Peter R.、Walker, Richard T.

  DOI：——

  日期：——
• 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.