1-(4-methoxytrityl)-4-piperidyl 2-cyanoethyl N,N-diisopropylphosphoramidite | 321862-15-1

• 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: 1-(4-methoxytrityl)-4-piperidyl 2-cyanoethyl N,N-diisopropylphosphoramidite
• 英文别名: 2-Cyanoethyl (1-((4-methoxyphenyl)diphenylmethyl)piperidin-4-yl) diisopropylphosphoramidite；3-[[di(propan-2-yl)amino]-[1-[(4-methoxyphenyl)-diphenylmethyl]piperidin-4-yl]oxyphosphanyl]oxypropanenitrile
• CAS: 321862-15-1
• 化学式: C₃₄H₄₄N₃O₃P
• 分子量: 573.715
• InChiKey: BKZHWXMMOQNHIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-methoxytrityl)-4-piperidyl 2-cyanoethyl N,N-diisopropylphosphoramidite 、 5(6)-羧基四甲基罗丹明琥珀酰亚胺酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [1-[3',6'-bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carbonyl]piperidin-4-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  A Tetramethyl Rhodamine (Tamra) Phosphoramidite Facilitates Solid-Phase-Supported Synthesis of 5‘-Tamra DNA

  摘要：

  6-Carboxy Tamra 1 was conjugated to:4-hydroxypiperidine with BOP and N-methylmorpholine, and the resulting 5-(N-pipyridyl-4-hydroxy)-Tamra carboxamide 2 was treated with 2-cyanoethyl tetraisopropylphosphorodiamidite to give 5- [N-pipyridyl-4-O-(2-cyanoethyl diisopropylphosphoramidite)]-Tamra carboxamide 3. Solutions of 3 were coupled onto the 5'-hydroxyl of solid-phase-supported DNA fragments with standard amidite coupling techniques. Cleavage and deprotection with aqueous tert-butylamine cocktail gave 5-Tamra-functionalized DNA as well as an additional compound without the Tamra chromophore. A mass spectrum of this product showed the incorporation of tert-butylamine.: The extra product was completely suppressed by including a 5 min acetylation step after coupling. A model study of 3 coupled onto thymidine-functionalized CPG showed similar results. NMR and mass spectra of cleaved products confirmed;the addition of tert-butylamine to the minor product. Coupling a Tamra active ester onto T CPG; which was previously coupled with N-(4-methoxytrityl)piperidyl-4-O-(2-cyanoethyl diisopropylphosphoramidite) A produced. the same major Tamra-bearing product, which coeluted on reverse phase HPLC with the major product generated with 3.

  DOI：

  10.1021/jo0011134
• 作为产物：
  描述：

  4-甲氧基三苯基氯甲烷 在 四氮唑 、 二异丙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(4-methoxytrityl)-4-piperidyl 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  A Tetramethyl Rhodamine (Tamra) Phosphoramidite Facilitates Solid-Phase-Supported Synthesis of 5‘-Tamra DNA

  摘要：

  6-Carboxy Tamra 1 was conjugated to:4-hydroxypiperidine with BOP and N-methylmorpholine, and the resulting 5-(N-pipyridyl-4-hydroxy)-Tamra carboxamide 2 was treated with 2-cyanoethyl tetraisopropylphosphorodiamidite to give 5- [N-pipyridyl-4-O-(2-cyanoethyl diisopropylphosphoramidite)]-Tamra carboxamide 3. Solutions of 3 were coupled onto the 5'-hydroxyl of solid-phase-supported DNA fragments with standard amidite coupling techniques. Cleavage and deprotection with aqueous tert-butylamine cocktail gave 5-Tamra-functionalized DNA as well as an additional compound without the Tamra chromophore. A mass spectrum of this product showed the incorporation of tert-butylamine.: The extra product was completely suppressed by including a 5 min acetylation step after coupling. A model study of 3 coupled onto thymidine-functionalized CPG showed similar results. NMR and mass spectra of cleaved products confirmed;the addition of tert-butylamine to the minor product. Coupling a Tamra active ester onto T CPG; which was previously coupled with N-(4-methoxytrityl)piperidyl-4-O-(2-cyanoethyl diisopropylphosphoramidite) A produced. the same major Tamra-bearing product, which coeluted on reverse phase HPLC with the major product generated with 3.

  DOI：

  10.1021/jo0011134

文献信息

• [EN] ANTISENSE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ANTISENS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2016044828A1

  公开（公告）日：2016-03-24

  The present disclosure provides oligomeric compounds. The present disclosure provides metabolically stable linkers that do not rapidly degrade in vivo. In certain embodiments, the present disclosure provides metabolically stable linkers for use in attaching a conjugate group to an oligonucleotide.

  本公开提供寡聚化合物。本公开提供代谢稳定的连接剂，在体内不会迅速降解。在某些实施例中，本公开提供代谢稳定的连接剂，用于将共轭基团连接到寡核苷酸上。
• ANTISENSE COMPOUNDS AND USES THEREOF
  申请人：Ionis Pharmaceuticals, Inc.

  公开号：US20180010126A1

  公开（公告）日：2018-01-11

  The present disclosure provides oligomeric compounds. The present disclosure provides metabolically stable linkers that do not rapidly degrade in vivo. In certain embodiments, the present disclosure provides metabolically stable linkers for use in attaching a conjugate group to an oligonucleotide.
• A Tetramethyl Rhodamine (Tamra) Phosphoramidite Facilitates Solid-Phase-Supported Synthesis of 5‘-Tamra DNA
  作者：Matthew H. Lyttle、Timothy G. Carter、Daren J. Dick、Ronald M. Cook

  DOI：10.1021/jo0011134

  日期：2000.12.1

  6-Carboxy Tamra 1 was conjugated to:4-hydroxypiperidine with BOP and N-methylmorpholine, and the resulting 5-(N-pipyridyl-4-hydroxy)-Tamra carboxamide 2 was treated with 2-cyanoethyl tetraisopropylphosphorodiamidite to give 5- [N-pipyridyl-4-O-(2-cyanoethyl diisopropylphosphoramidite)]-Tamra carboxamide 3. Solutions of 3 were coupled onto the 5'-hydroxyl of solid-phase-supported DNA fragments with standard amidite coupling techniques. Cleavage and deprotection with aqueous tert-butylamine cocktail gave 5-Tamra-functionalized DNA as well as an additional compound without the Tamra chromophore. A mass spectrum of this product showed the incorporation of tert-butylamine.: The extra product was completely suppressed by including a 5 min acetylation step after coupling. A model study of 3 coupled onto thymidine-functionalized CPG showed similar results. NMR and mass spectra of cleaved products confirmed;the addition of tert-butylamine to the minor product. Coupling a Tamra active ester onto T CPG; which was previously coupled with N-(4-methoxytrityl)piperidyl-4-O-(2-cyanoethyl diisopropylphosphoramidite) A produced. the same major Tamra-bearing product, which coeluted on reverse phase HPLC with the major product generated with 3.