2-(N-tert-butylhydroxylamino)-6-chloro-9-(2',3'-O-isopropylidene-5'-O-triphenylmethyl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(N-tert-butylhydroxylamino)-6-chloro-9-(2',3'-O-isopropylidene-5'-O-triphenylmethyl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine
• 英文别名: N-[9-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloro-8-tri(propan-2-yl)silylpurin-2-yl]-N-tert-butylhydroxylamine
• 化学式: C₄₅H₅₈ClN₅O₅Si
• 分子量: 812.525
• InChiKey: PVTOJMDMYDCTLY-KPASRLDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.79
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(N-tert-butylhydroxylamino)-6-chloro-9-(2',3'-O-isopropylidene-5'-O-triphenylmethyl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以99%的产率得到2-(N-tert-butylacetoxylamino)-6-chloro-9-(2',3'-O-isopropylidene-5'-O-triphenylmethyl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine
  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：

  亚硝基叔丁烷 、 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以75%的产率得到2-(N-tert-butylhydroxylamino)-6-chloro-9-(2',3'-O-isopropylidene-5'-O-triphenylmethyl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine
  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