2-(N-tert-butylacetoxyamino)-2'-deoxyadenosine | 855860-84-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-(N-tert-butylacetoxyamino)-2'-deoxyadenosine
• 英文别名: Adenosine, 2-[(acetyloxy)(1,1-dimethylethyl)amino]-2a(2)-deoxy-；[[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-tert-butylamino] acetate
• CAS: 855860-84-3
• 化学式: C₁₆H₂₄N₆O₅
• 分子量: 380.404
• InChiKey: ZVGHMCKTIUUQAY-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  148.85
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(N-tert-butylacetoxyamino)-2'-deoxyadenosine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到2-(N-tert-butylhydroxylamino)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and EPR Studies of 2-N-tert-Butylaminoxylpurine Derivatives

  摘要：

  2'-Deoxyribofuranosylpurine derivatives bearing an N-tert-butylaminoxyl group (1a and 2a) were synthesized via oxidation of the corresponding N-tert-butylhydroxylamines (1b and 2b), which were synthesized by lithiation of 8-TIPS-6-chloropurine (3) at the 2-position and the following reaction with 2-methyl-2-nitrosopropane. Treatment of 1b and 2b with 1 equiv of NalO(4) resulted in efficient formation of la and 2a. which were isolated as purple and red solids, respectively. The EPR spectra of la showed pH dependency due to structural change of purine moiety.

  DOI：

  10.1021/ol047668t
• 作为产物：
  描述：

  [[9-[(6aR,8R,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-6-aminopurin-2-yl]-tert-butylamino] acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以74%的产率得到2-(N-tert-butylacetoxyamino)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and EPR Studies of 2-N-tert-Butylaminoxylpurine Derivatives

  摘要：

  2'-Deoxyribofuranosylpurine derivatives bearing an N-tert-butylaminoxyl group (1a and 2a) were synthesized via oxidation of the corresponding N-tert-butylhydroxylamines (1b and 2b), which were synthesized by lithiation of 8-TIPS-6-chloropurine (3) at the 2-position and the following reaction with 2-methyl-2-nitrosopropane. Treatment of 1b and 2b with 1 equiv of NalO(4) resulted in efficient formation of la and 2a. which were isolated as purple and red solids, respectively. The EPR spectra of la showed pH dependency due to structural change of purine moiety.

  DOI：

  10.1021/ol047668t