2',5'-dideoxy-5'-(2-hydroxyethylthio)-3'-O-(diphenyl-tert-butylsilyl)-N²-isobutyrylguanosine | 153765-16-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',5'-dideoxy-5'-(2-hydroxyethylthio)-3'-O-(diphenyl-tert-butylsilyl)-N²-isobutyrylguanosine
• CAS: 153765-16-3
• 化学式: C₃₂H₄₁N₅O₅SSi
• 分子量: 635.86
• InChiKey: VHTWAVDTYXRPTD-JIMJEQGWSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131.36
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2',5'-dideoxy-5'-(2-hydroxyethylthio)-3'-O-(diphenyl-tert-butylsilyl)-N²-isobutyrylguanosine 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3'-O-(P-β-cyanoethoxy-N,N-diisopropylaminophosphinyl)-2',5'-dideoxy-5'-(2-O-4,4'-dimethoxytritylthio)-N²-isobutyrylguanosine
  参考文献：
  名称：

  Synthesis of Triple Helix Forming Oligonucleotides with a Stretched Phosphodiester Backbone

  摘要：

  Total synthesis of novel DMT-phosphoramidites of thymidine (11 and 15) and 2'-deoxyguanosine (8 and 20) have been accomplished. The utility of these modified building blocks in the preparation of triple helix forming oligodeoxyribonucleotides with a stretched phosphodiester backbone has been evaluated. It was found that the oligonucleotides with extended backbones were unable to enhance the binding to duplex targets containing CG or TA base pairs.

  DOI：

  10.1080/15257779408013239
• 作为产物：
  描述：

  N²-isobutyryl-3'-O-t-butyldiphenylsilyl-5'-iodo-2',5'-dideoxyguanosine 、 2-mercaptoethanol sodium salt 以 1,4-二氧六环 为溶剂， 反应 3.5h， 以86.5%的产率得到2',5'-dideoxy-5'-(2-hydroxyethylthio)-3'-O-(diphenyl-tert-butylsilyl)-N²-isobutyrylguanosine
  参考文献：
  名称：

  Synthesis of Triple Helix Forming Oligonucleotides with a Stretched Phosphodiester Backbone

  摘要：

  Total synthesis of novel DMT-phosphoramidites of thymidine (11 and 15) and 2'-deoxyguanosine (8 and 20) have been accomplished. The utility of these modified building blocks in the preparation of triple helix forming oligodeoxyribonucleotides with a stretched phosphodiester backbone has been evaluated. It was found that the oligonucleotides with extended backbones were unable to enhance the binding to duplex targets containing CG or TA base pairs.

  DOI：

  10.1080/15257779408013239

文献信息

• Synthesis of triple helix forming oligonucleotides with a stretched phosphodiester backbone
  作者：T. Sudhakar Rao、K. Jayaraman、Ganapathi R. Revankar

  DOI：10.1016/s0040-4039(00)73706-3

  日期：1993.9