3-[[1-[3',6'-Bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carbonyl]piperidin-4-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile | 321862-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-[[1-[3',6'-Bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carbonyl]piperidin-4-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 321862-13-9
• 化学式: C₃₉H₄₈N₅O₆P
• 分子量: 713.814
• InChiKey: UVLQWZNHBVWNDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[[1-[3',6'-Bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carbonyl]piperidin-4-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile 、 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：

  5-羧基四甲基罗丹明 在 N-甲基吗啉 、 四氮唑 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.25h， 生成 3-[[1-[3',6'-Bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carbonyl]piperidin-4-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  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

• 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.