2'-O-acetylthiomethyl-5'-O-(4,4'-dimethoxytrityl)uridine | 910028-93-2

• 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: 2'-O-acetylthiomethyl-5'-O-(4,4'-dimethoxytrityl)uridine
• 英文别名: 2′-O-acetylthiomethyl-5′-O-(4,4′-dimethoxytrityl)uridine；S-[[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxymethyl] ethanethioate
• CAS: 910028-93-2
• 化学式: C₃₃H₃₄N₂O₉S
• 分子量: 634.707
• InChiKey: DYTQYDAEKISNSP-PMFUCWTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O-acetylthiomethyl-5'-O-(4,4'-dimethoxytrityl)uridine 在 二氯乙酸 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.04h， 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 吡啶 、 磺酰氯 、 18-冠醚-6 、 乙酸酐 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2'-O-acetylthiomethyl-5'-O-(4,4'-dimethoxytrityl)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

文献信息

• A versatile post-synthetic method on a solid support for the synthesis of RNA containing reduction-responsive modifications
  作者：Annabelle Biscans、Sonia Rouanet、Jean-Jacques Vasseur、Christelle Dupouy、Françoise Debart

  DOI：10.1039/c6ob01272h

  日期：——

  post-synthetic method on a solid support was developed to introduce various disulfide bond containing groups at the 2′-OH of oligoribonucleotides (RNAs). It is based on a thiol disulfide exchange reaction between several readily accessible alkyldisulfanyl-pyridine derivatives and 2′-O-acetylthiomethyl RNA in the presence of butylamine. By this strategy, diverse 2′-O-alkyldithiomethyl RNAs were obtained

  开发了一种在固相支持物上的原始后合成方法，以在寡核糖核苷酸（RNA）的2'-OH处引入各种含二硫键的基团。它基于丁胺存在下几种易于获得的烷基二硫烷基-吡啶衍生物与2'- O-乙酰硫基甲基RNA之间的硫醇二硫键交换反应。通过这种策略，获得了多种2'- O-烷基二硫甲基RNA。这些修饰提供了对RNA的高核酸酶抗性，并可以通过谷胱甘肽处理轻松去除，因此具有潜在的siRNA前药用途。
• First Evaluation of Acyloxymethyl or Acylthiomethyl Groups as Biolabile 2‘-<i>O</i>-Protections of RNA
  作者：Nora Parey、Carine Baraguey、Jean-Jacques Vasseur、Françoise Debart

  DOI：10.1021/ol0616182

  日期：2006.8.1

  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.