2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-N6-benzoyl-adenosine | 1219089-97-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-N6-benzoyl-adenosine
• CAS: 1219089-97-0
• 化学式: C₂₂H₂₄N₆O₇S₂
• 分子量: 548.601
• InChiKey: CEPHSBSFECQPBD-VGKBRBPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  169.0
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-N6-benzoyl-adenosine 在 N-甲基吗啉 作用下， 以 2-甲基四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 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
• 作为产物：
  描述：

  MrA(Bz)TCI 在 吡啶 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2'-O-(1,1-dioxo-1λ6-thiomorpholine-4-carbothioate)-N6-benzoyl-adenosine
  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。