N2-isobutyryl-O6-benzyl-8N-(4-methoxyphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine | 444594-36-9

• 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-O6-benzyl-8N-(4-methoxyphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
• 英文别名: N²-isobutyryl-O⁶-benzyl-8N-(4-methoxyphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
• CAS: 444594-36-9
• 化学式: C₄₀H₆₀N₆O₆Si₂
• 分子量: 777.124
• InChiKey: KUXYFFLSKKCHJH-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.45
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  130.88
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N2-isobutyryl-O6-benzyl-8N-(4-methoxyphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 6.0h， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-(4-methoxyanilino)-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：

  3',5'-O,O'-bis(tert-butyldimethylsilyl)-8-bromo-2'-deoxyguanosine 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 偶氮二甲酸二异丙酯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 反应 52.0h， 生成 N2-isobutyryl-O6-benzyl-8N-(4-methoxyphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
  参考文献：
  名称：

  Highly Efficient Synthesis of a Phosphoramidite Building Block of C8-Deoxyguanosine Adducts of Aromatic Amines

  摘要：

  描述了5′-O-DMTr-3′-O-磷酰胺-衍生的C8-芳胺-dG加合物11和12的合成。这些化合物是自动合成位点特异性改性寡核苷酸的潜在构建块。C8-加合物是通过钯催化的交叉耦合反应合成的。

  DOI：

  10.1055/s-2002-25354

文献信息

• Synthesis of Oligonucleotide Building Blocks of 2′-Deoxyguanosine Bearing a C8-Arylamine Modification
  作者：S. Gräsl、C. Meier

  DOI：10.1081/ncn-120022751

  日期：2003.10

  C8-Arylamine-dG adducts were synthesized by palladium-catalyzed cross-coupling reactions. The corresponding 5'-O-DMTr-3'-O-phosphoramidite-C8-arylamine-dG adducts were synthesized as potential building blocks for the automated synthesis of site-specifically modified oligonucleotides.