2'-O-(morpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-uridine-3'-O-(β-cyanoethyl)-N,N-diisopropyl-phosphoramidite | 1219089-75-4

• 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-(morpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-uridine-3'-O-(β-cyanoethyl)-N,N-diisopropyl-phosphoramidite
• 英文别名: O-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] morpholine-4-carbothioate
• CAS: 1219089-75-4
• 化学式: C₄₄H₅₄N₅O₁₀PS
• 分子量: 875.98
• InChiKey: GHTZOOZQBBIHJV-JEVDOWJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  61
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-1-imidazole thionocarbamate 在 N-甲基吗啉 、 吡啶 、 氢氟酸 作用下， 以 2-甲基四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 2'-O-(morpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-uridine-3'-O-(β-cyanoethyl)-N,N-diisopropyl-phosphoramidite
  参考文献：
  名称：

  Streamlined Process for the Chemical Synthesis of RNA Using 2′-O-Thionocarbamate-Protected Nucleoside Phosphoramidites in the Solid Phase

  摘要：

  An improved method for the chemical synthesis of RNA was developed utilizing a streamlined method for the preparation of phosphoramidite monomers and a single-step deprotection of the resulting oligoribo-nucleotide product using 1,2-diamines under anhydrous conditions. The process is compatible with most standard heterobase protection and employs a 2'-O-(1,1-dioxo-1 lambda(6)-thiomorpholine-4-carbothioate) as a unique 2'-hydroxyl protective group. Using this approach, it was demonstrated that the chemical synthesis of RNA can be as simple and robust as the chemical synthesis of DNA.

  DOI：

  10.1021/ja201561z

文献信息

• PROTECTED MONOMER AND METHOD OF FINAL DEPROTECTION FOR RNA SYNTHESIS
  申请人：Dellinger Douglas J.

  公开号：US20100076183A1

  公开（公告）日：2010-03-25

  A nucleoside monomer that is protected by a thionocarbamate protecting group is provided, as well as a method for making a polynucleotide that uses the same. Also provided is a polynucleotide synthesis method that employs a diamine to deprotect a protected polynucleotide.

  提供了一种由硫代氨基甲酸酯保护基保护的核苷单体，以及使用该核苷单体制备多核苷酸的方法。还提供了一种利用二胺去保护受保护多核苷酸的多核苷酸合成方法。
• Streamlined Process for the Chemical Synthesis of RNA Using 2′-<i>O</i>-Thionocarbamate-Protected Nucleoside Phosphoramidites in the Solid Phase
  作者：Douglas J. Dellinger、Zoltán Timár、Joel Myerson、Agnieszka B. Sierzchala、John Turner、Fernando Ferreira、Zoltán Kupihár、Geraldine Dellinger、Kenneth W. Hill、James A. Powell、Jeffrey R. Sampson、Marvin H. Caruthers

  DOI：10.1021/ja201561z

  日期：2011.8.3

  An improved method for the chemical synthesis of RNA was developed utilizing a streamlined method for the preparation of phosphoramidite monomers and a single-step deprotection of the resulting oligoribo-nucleotide product using 1,2-diamines under anhydrous conditions. The process is compatible with most standard heterobase protection and employs a 2'-O-(1,1-dioxo-1 lambda(6)-thiomorpholine-4-carbothioate) as a unique 2'-hydroxyl protective group. Using this approach, it was demonstrated that the chemical synthesis of RNA can be as simple and robust as the chemical synthesis of DNA.