N²-isobutyryl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine | 919530-66-8

• 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: N²-isobutyryl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• 英文别名: N-[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-(4-methylanilino)-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 919530-66-8
• 化学式: C₃₃H₅₄N₆O₅Si₂
• 分子量: 671.0
• InChiKey: ZBECENKKHXCOBH-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 5.0h， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-(4-methylanilino)-6-oxo-1H-purin-2-yl]-2-methylpropanamide
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Arylamine Adducts of Borderline Carcinogens

  摘要：

  C8-Arylamine-dG adducts of borderline carcinogens and the bladder and breast carcinogen 4-amino-biphenyl were prepared using cross-coupling chemistry. These adducts were converted into the corresponding C8-arylamine-5'-O-DMTr-2'-deoxyguanosine phosphoramidites and then used as building blocks for automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were characterized by UV melting temperature analysis, enzymatic digestion, and circular dichroism.

  DOI：

  10.1021/jo061803t
• 作为产物：
  描述：

  O⁶-benzyl-8-bromo-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine 在 palladium on activated charcoal potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 吡啶 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 52.0h， 生成 N²-isobutyryl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Arylamine Adducts of Borderline Carcinogens

  摘要：

  C8-Arylamine-dG adducts of borderline carcinogens and the bladder and breast carcinogen 4-amino-biphenyl were prepared using cross-coupling chemistry. These adducts were converted into the corresponding C8-arylamine-5'-O-DMTr-2'-deoxyguanosine phosphoramidites and then used as building blocks for automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were characterized by UV melting temperature analysis, enzymatic digestion, and circular dichroism.

  DOI：

  10.1021/jo061803t