2'-O-(triisopropylsilyl)uridine | 54925-72-3

• 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: 2'-O-(triisopropylsilyl)uridine
• 英文别名: 2'-TIPS-uridine；O^2'-triisopropylsilanyl-uridine；1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-tri(propan-2-yl)silyloxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 54925-72-3
• 化学式: C₁₈H₃₂N₂O₆Si
• 分子量: 400.547
• InChiKey: OUOOZPHUGYDNLH-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyluridine 3'-N,N-diisopropylmethyl phosphoramidite 、 2'-O-(triisopropylsilyl)uridine 在 4,5-二氰基咪唑 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  RNA synthesis via dimer and trimer phosphoramidite block coupling

  摘要：

  The solid-phase synthesis of oligoribonucleotides using dimer and trimer phosphoramidite blocks is described. This method significantly reduces the total number of steps required in the synthesis of a target RNA sequence, provides more material, and simplifies separation of the product from shorter failure sequences. The procedure is illustrated by the synthesis of UpU, ApA, and UpUpU phosphoramidite blocks and their use in the rapid synthesis of oligoribonucleotides on a solid support. Dimer and trimer amidite blocks will likely find use in the large scale solution (or solid)-phase synthesis of siRNA drugs. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.03.042
• 作为产物：
  描述：

  5’-O-(4,4’-二甲氧基三苯甲基)尿苷 在 吡啶 、 silver nitrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.16h， 生成 2'-O-(triisopropylsilyl)uridine
  参考文献：
  名称：

  RNA synthesis via dimer and trimer phosphoramidite block coupling

  摘要：

  The solid-phase synthesis of oligoribonucleotides using dimer and trimer phosphoramidite blocks is described. This method significantly reduces the total number of steps required in the synthesis of a target RNA sequence, provides more material, and simplifies separation of the product from shorter failure sequences. The procedure is illustrated by the synthesis of UpU, ApA, and UpUpU phosphoramidite blocks and their use in the rapid synthesis of oligoribonucleotides on a solid support. Dimer and trimer amidite blocks will likely find use in the large scale solution (or solid)-phase synthesis of siRNA drugs. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.03.042

文献信息

• A catalytic method for chemoselective detritylation of 5′-tritylated nucleosides under mild and heterogeneous conditions using silica sulfuric acid as a recyclable catalyst
  作者：Ali Khalafi-Nezhad、Abolfath Parhami、Mohammad Navid Soltani Rad、Mohammad Ali Zolfigol、Abdolkarim Zare

  DOI：10.1016/j.tetlet.2007.05.153

  日期：2007.7

  A rapid, mild and highly efficient procedure for the chemoselective deprotection of triphenylmethyl (trityl, Tr), p-anisyldiphenylmethyl (monomethoxytrityl, MMT) and di-(p-anisyl)phenylmethyl (dimethoxytrityl, DMT) groups from nucleoside trityl ethers has been established. The deprotection was achieved at room temperature, using a catalytic amount of silica sulfuric acid (SSA) in acetonitrile. The

  已经建立了一种快速，温和且高效的方法，用于从核苷三苯甲基醚中化学选择脱保护三苯基甲基（三苯甲基，Tr），对-茴香基二苯基甲基（单甲氧基三苯甲基，MMT）和二（对茴香基）苯基甲基（二甲氧基三苯甲基，DMT）基团。 。脱保护在室温下进行，使用催化量的乙腈中的二氧化硅硫酸（SSA）。三苯甲基核苷无需任何纯化即可在2-17分钟内脱保护。这些条件与其他对酸敏感的羟基保护基团相容，例如对-甲氧基苄基（PMB），异亚丙基，环己叉基，二-（对-茴香基）亚甲基，三异丙基甲硅烷基（TIPS）和叔丁基二甲基甲硅烷基（TBDMS）。
• Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups
  作者：Jih Ru Hwu、Moti L. Jain、Fu-Yuan Tsai、Shwu-Chen Tsay、Arumugham Balakumar、Gholam H. Hakimelahi

  DOI：10.1021/jo000024o

  日期：2000.8.1

  triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative study of deprotection reactions by utilization of CAN alone or CAN-SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN-SiO2 in the removal of these protective groups from organic

  发现硅胶负载的硝酸铈铵（CAN-SiO2）在温和条件下可从受保护的核苷和核苷酸中快速选择性地裂解三苯甲基（Tr），单甲氧基三苯甲基（MMTr）和二甲氧基三苯甲基（DMTr）基团。脱保护的效率取决于所得碳阳离子物质的稳定性：DMTr +> MMTr +> Tr +。使用催化量的这种固体负载的试剂还可以有效地和选择性地从核糖核苷的二或三甲硅烷基醚中的伯羟基官能团中除去叔丁基二甲基甲硅烷基或三异丙基甲硅烷基。通过单独使用CAN或CAN-SiO2进行脱保护反应的比较研究表明，涉及固相支持物的反应速率显着提高。
• RNA synthesis via dimer and trimer phosphoramidite block coupling
  作者：Matthew Hassler、Yi Qiao Wu、N. Mallikarjuna Reddy、Tak Hang Chan、Masad J. Damha

  DOI：10.1016/j.tetlet.2011.03.042

  日期：2011.5

  The solid-phase synthesis of oligoribonucleotides using dimer and trimer phosphoramidite blocks is described. This method significantly reduces the total number of steps required in the synthesis of a target RNA sequence, provides more material, and simplifies separation of the product from shorter failure sequences. The procedure is illustrated by the synthesis of UpU, ApA, and UpUpU phosphoramidite blocks and their use in the rapid synthesis of oligoribonucleotides on a solid support. Dimer and trimer amidite blocks will likely find use in the large scale solution (or solid)-phase synthesis of siRNA drugs. (C) 2011 Elsevier Ltd. All rights reserved,