N-{9-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-benzamide | 917598-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-{9-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-benzamide
• CAS: 917598-80-2
• 化学式: C₃₃H₃₅N₅O₃Si
• 分子量: 577.758
• InChiKey: RLZSAERREBGQQH-UIOOFZCWSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-{9-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-benzamide 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以0.50 g的产率得到6-N-benzoyl-1',3'-dideoxy-2'-isoadenosine
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703
• 作为产物：
  描述：

  6-N-benzoyl-5'-O-(t-butyldiphenylsilyl)-1'-deoxy-2'-isoadenosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 6.0h， 生成 N-{9-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-benzamide
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703