4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3-methoxybiphenyl | 912818-50-9

• 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-methoxybiphenyl
• CAS: 912818-50-9
• 化学式: C₃₉H₃₈O₆
• 分子量: 602.727
• InChiKey: OBSSOLTTXBSYKE-YXWIYCFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3-methoxybiphenyl 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-3''-O-(2-cyanoethyl-N,N'-diisopropylaminophosphino)-β-D-ribofuranosyl]-3-methoxybiphenyl
  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：

  1β-(4-bromophenyl)-1,2-dideoxy-D-ribofuranose 在 palladium diacetate 吡啶 、 4-二甲氨基吡啶 、 potassium fluoride 、 potassium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3-methoxybiphenyl
  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