3'-O-(2-azidomethlbenzoyl)-2'-O-TBDMS-uridine | 1384164-34-4

• 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-azidomethlbenzoyl)-2'-O-TBDMS-uridine
• CAS: 1384164-34-4
• 化学式: C₂₃H₃₁N₅O₇Si
• 分子量: 517.614
• InChiKey: GVVAJJMRVTVDJX-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  168.61
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-O-(2-azidomethlbenzoyl)-2'-O-TBDMS-uridine 、 5'-O-DMTr-2'-O-TBDMS-uridine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 在 吡啶 、 苯甲基-2-磺酰三硝基三氮唑 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 以82%的产率得到OH[UU]AZMB
  参考文献：
  名称：

  Chemical synthesis of bioactive siRNA in solution phase by using 2-(azidomethyl)benzoyl as 3′-hydroxyl group protecting group

  摘要：

  A protecting group AZMB was introduced to ribonucleosides 3'-hydroxyl group to facilitate solution phase synthesis of siRNA. The protection and cleavage reaction were carried out in mild conditions, that is protection by acyl chloride and cleavage by triphenylphosphine. The synthesized siRNA showed good biological activity to suppress targeted superoxide dismutase gene expression. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.027
• 作为产物：
  描述：

  邻甲基苯甲酸甲酯 在 N-甲基咪唑 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium azide 、 对甲苯磺酸 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 3'-O-(2-azidomethlbenzoyl)-2'-O-TBDMS-uridine
  参考文献：
  名称：

  Chemical synthesis of bioactive siRNA in solution phase by using 2-(azidomethyl)benzoyl as 3′-hydroxyl group protecting group

  摘要：

  A protecting group AZMB was introduced to ribonucleosides 3'-hydroxyl group to facilitate solution phase synthesis of siRNA. The protection and cleavage reaction were carried out in mild conditions, that is protection by acyl chloride and cleavage by triphenylphosphine. The synthesized siRNA showed good biological activity to suppress targeted superoxide dismutase gene expression. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.027

文献信息

• METHOD FOR PREPARING OLIGONUCLEOTIDE
  申请人：Xi Zhen

  公开号：US20110237786A1

  公开（公告）日：2011-09-29

  A method for preparing oligonucleotide comprising reacting the compound of Formula (1) with the compound of Formula (2) in a liquid reaction medium under the condition of condensation reaction to obtain the compound of formula (3). In the method according to the present invention, the functional groups are protected by suitable protective groups to only expose the 5′-OH of the compound of Formula (1) (OH-component) and the 3′-phosphate of the compound of Formula (2) (P-component) which are to be connected, so that the condensation reaction is carried out in a liquid reaction medium to bond the OH-component and P-component to obtain DNA or RNA short chain. The method of the present invention does not need a solid phase column and can be carried out in a liquid reaction medium. Thus, oligonucleotides can be synthesized on a large scale.

  一种制备寡核苷酸的方法，包括在液体反应介质中，将化合物式（1）与化合物式（2）在缩合反应条件下反应，以获得化合物式（3）。根据本发明的方法，通过适当的保护基保护功能基团，仅暴露化合物式（1）的5'-OH（OH组分）和化合物式（2）的3'-磷酸酯（P组分），这两者将被连接，从而在液体反应介质中进行缩合反应，将OH组分和P组分连接以获得DNA或RNA短链。本发明的方法不需要固相柱，并且可以在液体反应介质中进行。因此，寡核苷酸可以大规模合成。