3'-O-[2-(trimethylsilyl)benzoyl]thymidine | 1146309-83-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-[2-(trimethylsilyl)benzoyl]thymidine
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-trimethylsilylbenzoate
• CAS: 1146309-83-2
• 化学式: C₂₀H₂₆N₂O₆Si
• 分子量: 418.522
• InChiKey: QUAYQWOCKDCURP-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-[2-(trimethylsilyl)benzoyl]thymidine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 、 二异丙胺 作用下， 以42%的产率得到[(2R,3S,5R)-2-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-trimethylsilylbenzoate
  参考文献：
  名称：

  Synthesis and biochemical properties of oligodeoxynucleotides acylated by the chemically stable 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5′ or 3′ terminus

  摘要：

  Oligodeoxynucleotides acylated with a 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5' or 3' terminus were synthesized according to the general method used for DNA synthesis. The acylated DNA oligomers could be easily purified due to the high lipophilicity of the TMSBz group and showed enhanced hybridization ability and resistance to exonucleases. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.121
• 作为产物：
  描述：

  [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-trimethylsilylbenzoate 在 sodium trichloroacetate 作用下， 以 二氯甲烷 为溶剂， 生成 3'-O-[2-(trimethylsilyl)benzoyl]thymidine
  参考文献：
  名称：

  Synthesis and biochemical properties of oligodeoxynucleotides acylated by the chemically stable 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5′ or 3′ terminus

  摘要：

  Oligodeoxynucleotides acylated with a 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5' or 3' terminus were synthesized according to the general method used for DNA synthesis. The acylated DNA oligomers could be easily purified due to the high lipophilicity of the TMSBz group and showed enhanced hybridization ability and resistance to exonucleases. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.121

文献信息

• Synthesis and biochemical properties of oligodeoxynucleotides acylated by the chemically stable 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5′ or 3′ terminus
  作者：Ken Yamada、Haruhiko Taguchi、Akihiro Ohkubo、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.tetlet.2010.07.121

  日期：2010.9

  Oligodeoxynucleotides acylated with a 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5' or 3' terminus were synthesized according to the general method used for DNA synthesis. The acylated DNA oligomers could be easily purified due to the high lipophilicity of the TMSBz group and showed enhanced hybridization ability and resistance to exonucleases. (c) 2010 Elsevier Ltd. All rights reserved.