1-((1R,6R,8R,9S)-6-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-9-hydroxy-2,5,7-trioxabicyclo[4.2.1]nonan-8-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1446748-47-5

• 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: 1-((1R,6R,8R,9S)-6-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-9-hydroxy-2,5,7-trioxabicyclo[4.2.1]nonan-8-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 1446748-47-5
• 化学式: C₃₃H₃₄N₂O₉
• 分子量: 602.641
• InChiKey: MGQACPZTRTWKAI-NDYSUJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130.47
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-((1R,6R,8R,9S)-6-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-9-hydroxy-2,5,7-trioxabicyclo[4.2.1]nonan-8-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 、 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 二氯甲烷 为溶剂， 以84%的产率得到3-[[(1R,6R,8R,9S)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-8-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5,7-trioxabicyclo[4.2.1]nonan-9-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Synthesis and Properties of 2′-O,4′-C-Ethyleneoxy Bridged 5-Methyluridine

  摘要：

  2'-O,4'-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4'-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stranded RNA and triplexes with double-stranded DNA relative to the natural oligonucleotide and oligonucleotides modified by another seven-membered bridged 5-methyluridine, 2',4'-BNA(coc)-T. In addition, EoNA-T showed excellent nuclease resistance.

  DOI：

  10.1021/ol401566r
• 作为产物：
  描述：

  5-甲基尿甙 在 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 20% palladium hydroxide-activated charcoal 、 四丁基氟化铵 、 碘 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 、 三苯基膦 、 silver(l) oxide 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 1-((1R,6R,8R,9S)-6-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-9-hydroxy-2,5,7-trioxabicyclo[4.2.1]nonan-8-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Properties of 2′-O,4′-C-Ethyleneoxy Bridged 5-Methyluridine

  摘要：

  2'-O,4'-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4'-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stranded RNA and triplexes with double-stranded DNA relative to the natural oligonucleotide and oligonucleotides modified by another seven-membered bridged 5-methyluridine, 2',4'-BNA(coc)-T. In addition, EoNA-T showed excellent nuclease resistance.

  DOI：

  10.1021/ol401566r