1,3,5-tris-<9-<2'-deoxythymidin-3'-O-yl>-2,5-diaza-1,6,9-trioxononyl>benzene | 221898-84-6

• 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: 1,3,5-tris-<9-<2'-deoxythymidin-3'-O-yl>-2,5-diaza-1,6,9-trioxononyl>benzene
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-[2-[[3,5-bis[2-[[4-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-4-oxobutanoyl]amino]ethylcarbamoyl]benzoyl]amino]ethylamino]-4-oxobutanoate
• CAS: 221898-84-6
• 化学式: C₅₇H₇₂N₁₂O₂₄
• 分子量: 1309.26
• InChiKey: MELRLPQZQVCCLZ-GCABMJPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  93
• 可旋转键数：
  33
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  490
• 氢给体数：
  12
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-N2-isobutyryl-2'-deoxyguanosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 、 1,3,5-tris-<9-<2'-deoxythymidin-3'-O-yl>-2,5-diaza-1,6,9-trioxononyl>benzene 在 四氮唑 、 叔丁基过氧化氢 、 二叔丁基过氧化物 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  The use of liquid phase carriers for large scale oligonucleotide synthesis in solution via phosphoamidite chemistry

  摘要：

  Nucleoside derivatives coupled to a multifunctional highly symmetric primary amine 3 built the fundamental of a convenient method for large scale oligonucleotide synthesis in solution. The basic purification for the fast isolation of intermediates is obtained by gel permeation chromatography. Monomer and dimer phosphoamidites (1a-d; 2a,b) are used for the preparation of short oligodeoxynucleotides. Total cycle yields between 81 and 95 % and average cycle yields of 87 % were obtained. MALDI-TOF-mass spectrometry was used for the analysis of the fully protected intermediates during synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00059-9
• 作为产物：
  描述：

  1,3,5-tris-<2,5-diaza-9-<5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-deoxythymidine-3'-O-yl>-1,6,9-trioxononyl>benzene 在 三氟乙酸 作用下， 以 甲醇 、 硝基甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.03h， 以97%的产率得到1,3,5-tris-<9-<2'-deoxythymidin-3'-O-yl>-2,5-diaza-1,6,9-trioxononyl>benzene
  参考文献：
  名称：

  The use of liquid phase carriers for large scale oligonucleotide synthesis in solution via phosphoamidite chemistry

  摘要：

  Nucleoside derivatives coupled to a multifunctional highly symmetric primary amine 3 built the fundamental of a convenient method for large scale oligonucleotide synthesis in solution. The basic purification for the fast isolation of intermediates is obtained by gel permeation chromatography. Monomer and dimer phosphoamidites (1a-d; 2a,b) are used for the preparation of short oligodeoxynucleotides. Total cycle yields between 81 and 95 % and average cycle yields of 87 % were obtained. MALDI-TOF-mass spectrometry was used for the analysis of the fully protected intermediates during synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00059-9

文献信息

• Synthesis of new liquid phase carriers for use in large scale oligonucleotide synthesis in solution
  作者：Ralf Wörl、Hubert Köster

  DOI：10.1016/s0040-4020(99)00058-7

  日期：1999.3

  The synthesis of multifunctional symmetric primary amines 4 and 8 and the covalent binding of 5'-O-dimethoxytrityl-deoxynucleoside derivatives to their amino groups (compound 5 and 9) is described. Different strategies for dedimethoxytritylation including the use of strong acidic ion exchangers or protic acids and modified silica gels and/or gel permeation chromatography are developed. The resulting liquid phase carriers 6 and 10 are suitable for large scale oligonucleotide synthesis in solution using phosphoamidites and gel permeation chromatography for fast isolation of intermediates. (C) 1999 Elsevier Science Ltd. All rights reserved.