4'-(2''-deoxy-β-D-ribofuranosyl)-3-nitrobiphenyl | 912818-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-(2''-deoxy-β-D-ribofuranosyl)-3-nitrobiphenyl
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-[4-(3-nitrophenyl)phenyl]oxolan-3-ol
• CAS: 912818-47-4
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: ZKRVCDNTSKKUEE-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-(2''-deoxy-β-D-ribofuranosyl)-3-nitrobiphenyl 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 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：

  2-deoxy-D-ribose 在 palladium diacetate 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 potassium fluoride 、 正丁基锂 、 tert-butyl-ammonium fluoride 、 三氟化硼乙醚 、 溴 、 potassium carbonate 、 溶剂黄146 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 175.5h， 生成 4'-(2''-deoxy-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

文献信息

• Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides
  作者：A ZAHN、C LEUMANN

  DOI：10.1016/j.bmc.2006.05.072

  日期：2006.9.15

  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.