5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine | 1262310-96-2

• 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: 5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
• 英文别名: 2-(benzylamino)-9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-1,7-dihydropurine-6,8-dione
• CAS: 1262310-96-2
• 化学式: C₃₈H₃₇N₅O₇
• 分子量: 675.741
• InChiKey: MAOKWZCIBMUUTQ-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到3'-O-[(diisopropylamino)-(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of N²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability

  摘要：

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.

  DOI：

  10.1021/jo102187y
• 作为产物：
  描述：

  2'-脱氧-8-(苯基甲氧基)-鸟苷 在 吡啶 、 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of N²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability

  摘要：

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.

  DOI：

  10.1021/jo102187y

文献信息

• Synthesis of <i>N</i>²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability
  作者：Arunkumar Kannan、Cynthia J. Burrows

  DOI：10.1021/jo102187y

  日期：2011.1.21

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.