4-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)-1-bromobenzene | 912818-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)-1-bromobenzene
• CAS: 912818-31-6
• 化学式: C₁₅H₁₇BrO₅
• 分子量: 357.201
• InChiKey: JJWLRCUCMGFZGM-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)-1-bromobenzene 在 palladium diacetate 吡啶 、 potassium fluoride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-3''-O-(2-cyanoethyl-N,N'-diisopropylaminophosphino)-β-D-ribofuranosyl]-3-nitrobiphenyl
  参考文献：
  名称：

  Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides

  摘要：

  We describe the synthesis of eight novel C-nucleosides in which the nucleobases are replaced by biphenyl residues that carry one or two electron donor (-OCH3,-NH2) or acceptor (-NO2) functional groups in the distal ring. These C-nucleosides were synthesized convergently and in high yields from a common bromophenyl-C-nucleoside precursor via Suzuki coupling with the respective boronic acids or esters. These nucleosides were subsequently converted into the corresponding phosphoramidite building blocks and efficiently incorporated into oligodeoxynucleotides by standard phosphoramidite chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.072
• 作为产物：
  描述：

  D-(+)-核糖酸-gamma-内酯 在 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 正丁基锂 、 tert-butyl-ammonium fluoride 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 4-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)-1-bromobenzene
  参考文献：
  名称：

  Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides

  摘要：

  We describe the synthesis of eight novel C-nucleosides in which the nucleobases are replaced by biphenyl residues that carry one or two electron donor (-OCH3,-NH2) or acceptor (-NO2) functional groups in the distal ring. These C-nucleosides were synthesized convergently and in high yields from a common bromophenyl-C-nucleoside precursor via Suzuki coupling with the respective boronic acids or esters. These nucleosides were subsequently converted into the corresponding phosphoramidite building blocks and efficiently incorporated into oligodeoxynucleotides by standard phosphoramidite chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.072