4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl | 912818-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl
• CAS: 912818-48-5
• 化学式: C₃₈H₃₄N₂O₉
• 分子量: 662.696
• InChiKey: GSOGGENPZCGXCV-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  143.43
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-3''-O-(2-cyanoethyl-N,N'-diisopropylaminophosphino)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl
  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：

  4'-(3'',5''-di-O-acetyl-2''-deoxy-β-D-ribofuranosyl)-3,5-dinitrobiphenyl 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl
  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