2'-O-pivaloylthiomethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine | 910028-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-pivaloylthiomethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
• CAS: 910028-87-4
• 化学式: C₂₇H₄₈N₂O₈SSi₂
• 分子量: 616.924
• InChiKey: JAILUPAJRXJPKQ-MSNJVRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  118.08
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2'-O-pivaloylthiomethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 在 吡啶 、 二氯乙酸 、 二异丙基铵盐四氮唑 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.04h， 生成
  参考文献：
  名称：

  First Evaluation of Acyloxymethyl or Acylthiomethyl Groups as Biolabile 2‘-O-Protections of RNA

  摘要：

  Short oligo-U sequences containing 2'-O-acyloxymethyl or acylthiomethyl groups as biolabile 2'-O-protections of RNA have been synthesized. These modified homouridylates are deprotected upon cellular esterase activation to release the parent RNA. They exhibit exceptional resistance to nuclease degradation, and the evaluation of their pairing properties shows that the 2'-acyloxymethyl groups do not prevent the duplex dsRNA formation. These biolabile 2'-modifications overcome the first hurdle to turn oligoribonucleotides into canditates for RNA interference drugs.

  DOI：

  10.1021/ol0616182
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 磺酰氯 、 15-冠醚-5 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2'-O-pivaloylthiomethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  First Evaluation of Acyloxymethyl or Acylthiomethyl Groups as Biolabile 2‘-O-Protections of RNA

  摘要：

  Short oligo-U sequences containing 2'-O-acyloxymethyl or acylthiomethyl groups as biolabile 2'-O-protections of RNA have been synthesized. These modified homouridylates are deprotected upon cellular esterase activation to release the parent RNA. They exhibit exceptional resistance to nuclease degradation, and the evaluation of their pairing properties shows that the 2'-acyloxymethyl groups do not prevent the duplex dsRNA formation. These biolabile 2'-modifications overcome the first hurdle to turn oligoribonucleotides into canditates for RNA interference drugs.

  DOI：

  10.1021/ol0616182