2'-O-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)uridine | 910028-94-3

• 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-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)uridine
• 英文别名: [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxymethyl 2,2-dimethylpropanoate
• CAS: 910028-94-3
• 化学式: C₃₆H₄₀N₂O₁₀
• 分子量: 660.721
• InChiKey: DDAPVEKQTSDALP-PYTKSMOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O-pivaloyloxymethyl-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 、 15-冠醚-5 、 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 6.0h， 生成 2'-O-pivaloyloxymethyl-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

• RNA-based boronate internucleosidic linkages: an entry into reversible templated ligation and loop formation
  作者：Alejandro Gimenez Molina、Ivan Barvik、Sabine Müller、Jean-Jacques Vasseur、Michael Smietana

  DOI：10.1039/c8ob02182a

  日期：——

  the synthesis of a 5′-boronoribonucleotidic phosphoramidite building block, its incorporation at the 5′ extremities of RNA sequences, and its ability to generate boronate internucleosidic linkages by RNA- and DNA-templated ligation. Moreover, melting denaturation studies also revealed that 5′-boronic acid ended RNA sequences are able to promote the formation of RNA loops in the presence of RNA templating

  能够控制超分子生物聚合物组装和拆卸的模板的使用是一种有吸引力的方法，其应用范围从设计新的生物聚合物到调节复杂的生物系统。因此，基于自组装核酸的系统具有构建定义明确且刺激响应的分子结构的实质潜力。我们在这里首次报告5'-硼核糖核苷酸亚磷酰胺构件的合成，在5'末端的RNA序列的掺入以及通过RNA和DNA模板连接产生硼酸核苷间键的能力。此外，熔融变性研究还表明，在存在RNA模板伴侣的情况下，5'-硼酸末端的RNA序列能够促进RNA环的形成。
• A Base-Labile Group for 2′-OH Protection of Ribonucleosides: A Major Challenge for RNA Synthesis
  作者：Thomas Lavergne、Jean-Rémi Bertrand、Jean-Jacques Vasseur、Françoise Debart

  DOI：10.1002/chem.200801392

  日期：2008.10.20
• PROCEDE DE SYNTHESE D'ARN PAR VOIE CHIMIQUE
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2303905B1

  公开（公告）日：2012-11-28
• Chemical RNA Synthesis Method
  申请人：Debart Françoise

  公开号：US20110275793A1

  公开（公告）日：2011-11-10

  The invention relates to a method for the chemical synthesis of RNA, comprising the following steps: a) bonding to a solid support of a monomer having formula (II) in which—X 1 is a dimethoxytrityl group,—X 6 is H or an OAc group or OX 3 , in which X 3 is a group having formula (A), in which X is O or S, R′ is H or CH 3 and R is selected from a linear or branched alkyl group at C 1 to C 4 and a R 1 —O—R 2 group in which R 1 is an alkyl group at C 1 to C 2 and R 2 is a CH 3 group or CH 2 CH 2 —O—CH 3 or aryl; b) assembly with the monomer having formula (II) bound to the support thereof obtained in step (a) of at least one monomer having formula (III) in which X 1 , Bp, X 3 are as defined for formula (II) and X 5 is a hydrogen phosphonate monoester or phosphoramidite group, preferably a 2-cyanoethyl-N,N-diisopropylphosphoramidite group, which is used to obtain a protected single-strand RNA bound to a support.
• US8536318B2
  申请人：——

  公开号：US8536318B2

  公开（公告）日：2013-09-17