2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyladenosine-3'-O-(β-cyanoethyl)-N,N-diisopropylphosphoramidite | 1219089-94-7

• 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-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyladenosine-3'-O-(β-cyanoethyl)-N,N-diisopropylphosphoramidite
• 英文别名: 2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-adenosine-3'-O-(β-cyanoethyl)-N,N-diisopropyl-phosphoramidite；DMT-2'O-TC-rA(bz) Phosphoramidite, configured for ABI；O-[(2R,3R,4R,5R)-2-(6-benzamidopurin-9-yl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-3-yl] 1,1-dioxo-1,4-thiazinane-4-carbothioate
• CAS: 1219089-94-7
• 化学式: C₅₂H₅₉N₈O₁₀PS₂
• 分子量: 1051.19
• InChiKey: CDNDGAZKHYLQRS-AEBGNYAMSA-N

物化性质

• 溶解度：
  乙腈:甲苯(1:1):soluble0.1Mat18°C,clear

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  73
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  242
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  N6-苯甲酰基-3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷二基腺苷 在 N-甲基吗啉 、 吡啶 、 4-二甲氨基吡啶 、 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 11.0h， 生成 2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyladenosine-3'-O-(β-cyanoethyl)-N,N-diisopropylphosphoramidite
  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.