N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidyl>-6-aminohexyl 2-cyanoethyl N,N-diisopropylphosphoramidite | 149624-99-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidyl>-6-aminohexyl 2-cyanoethyl N,N-diisopropylphosphoramidite
• 英文别名: tert-butyl 4-[(2S)-3-[6-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyhexylamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxopropyl]imidazole-1-carboxylate
• CAS: 149624-99-7
• 化学式: C₄₁H₅₇N₆O₇P
• 分子量: 776.913
• InChiKey: XPPXADYQHASWJS-PIOGJOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidyl>-6-aminohexyl 2-cyanoethyl N,N-diisopropylphosphoramidite 在 吡啶 、 四氮唑 、 ammonium hydroxide 、 碘 作用下， 反应 12.42h， 生成 5'-O-(4,4'-Dimethoxytriphenylmethyl)thymidin-3'-yl N⁶-L-histidyl-6-aminohexyl phosphate ammonium salt
  参考文献：
  名称：

  Synthesis and characterization of imidazoyl-linked synthons and 3'-conjugated thymidine derivatives

  摘要：

  The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3'-conjugated thymidine derivatives using 5'-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

  DOI：

  10.1021/jo00069a022
• 作为产物：
  描述：

  6-氨基-1-己醇 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.75h， 生成 N⁶-α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidyl>-6-aminohexyl 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and characterization of imidazoyl-linked synthons and 3'-conjugated thymidine derivatives

  摘要：

  The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3'-conjugated thymidine derivatives using 5'-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

  DOI：

  10.1021/jo00069a022

文献信息

• Synthesis and characterization of imidazoyl-linked synthons and 3'-conjugated thymidine derivatives
  作者：Nikolai N. Polushin、Ban Chin Chen、Lawrence W. Anderson、Jack S. Cohen

  DOI：10.1021/jo00069a022

  日期：1993.8

  The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3'-conjugated thymidine derivatives using 5'-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.