5-O-(二(4-甲氧基苯基)苯基甲基)-3-胸苷酸单(4-氯苯基)酯化合物与N,N-二乙基乙胺(1:1) | 65062-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 5-O-(二(4-甲氧基苯基)苯基甲基)-3-胸苷酸单(4-氯苯基)酯化合物与N,N-二乙基乙胺(1:1)
• 英文名称: 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate triethylammonium salt
• 英文别名: 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenylphosphate) triethylammonium salt；triethylammonium 5'-O-dimethoxytritylthymidine 3'-(p-chlorophenyl)phosphate；5'-O-(bis(4-methoxyphenyl)phenylmethyl)-3'-thymidylic acid, mono(4-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)；[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (4-chlorophenyl) hydrogen phosphate;N,N-diethylethanamine
• CAS: 65062-61-5
• 化学式: C₆H₁₅N*C₃₇H₃₆ClN₂O₁₀P
• 分子量: 836.319
• InChiKey: LAKJKVUHWWKNHX-CFNLNGMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-O-(二(4-甲氧基苯基)苯基甲基)-3-胸苷酸单(4-氯苯基)酯化合物与N,N-二乙基乙胺(1:1) 反应 20.08h， 生成 <(MeO)2Tr>TpTOAc
  参考文献：
  名称：

  Phosphorus-31 NMR study of the mechanism of activation and coupling reactions in the synthesis of oligodeoxyribonucleotides by the phosphotriester method

  摘要：

  DOI：

  10.1021/jo00199a039
• 作为产物：
  描述：

  5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorphenylcyanoethyl phosphate) 在 水 、 三乙胺 作用下， 以 吡啶 为溶剂， 生成 5-O-(二(4-甲氧基苯基)苯基甲基)-3-胸苷酸单(4-氯苯基)酯化合物与N,N-二乙基乙胺(1:1)
  参考文献：
  名称：

  Phosphorus-31 NMR study of the mechanism of activation and coupling reactions in the synthesis of oligodeoxyribonucleotides by the phosphotriester method

  摘要：

  DOI：

  10.1021/jo00199a039

文献信息

• Synthesis and properties of deoxyoligonucleotides containing putrescinylthymine (nucleosides and nucleotides. LXXVI).
  作者：TADAYUKI TAKEDA、KAZUYOSHI IKEDA、YOSHIHISA MIZUNO、TOHRU UEDA

  DOI：10.1248/cpb.35.3558

  日期：——

  Putrescinylthymidine was prepared by the reduction of the Schiff base formed from a 2'-deoxy-5-formyluridine derivative and N-phthaloylputrescine, followed by deprotection. The following deoxyoligonucleotides containing putrescinylthymine (TP) were synthesized; dodecathymidylic acids containing two to four TP residues, self-complementary decanucleotides (AAGAATTCTT) and dodecanucleotides (AGATAGCTATCT) in which T residues were partly replaced by TP, and related oligomers. Oligonucleotides containing TP were resistant to nuclease S1 digestion and were poor substrates to venom phosphodiesterase. The thermal stability (Tm) of the duplex structure of oligomers containing TP was not enhanced in spite of the expected electrostatic binding between the putrescinyl and phosphoryl residues, and was rather sequence-dependent.

  腐胺胸苷是通过从 2'-脱氧-5-甲酰尿苷衍生物和 N-邻苯二甲酰胺腐胺形成的希夫碱的还原反应制备的，随后进行去保护处理。合成了以下含有腐胺胸苷（TP）的脱氧寡核苷酸；含有两个到四个 TP 殘基的十二聚胸苷酸、自互补的十聚核苷酸（AAGAATTCTT）和十二聚核苷酸（AGATAGCTATCT），其中 T 残基部分被 TP 替代，以及相关的寡聚物。含有 TP 的寡核苷酸对核酸酶 S1 消化具抵抗性，并且是毒液磷酸二酯酶的劣质底物。尽管预计腐胺和磷酸残基之间存在静电结合，含有 TP 的寡聚物双链结构的热稳定性（Tm）并没有增强，而是相当依赖序列。
• A new solid phase approach for rapid syntheses of oligonucleotides bearing a 3′-terminal phosphate group
  作者：Eduard Felder、Robert Schwyzer、Ramamurthy Charubala、Wolfgang Pfleiderer、Bernd Schulz

  DOI：10.1016/0040-4039(84)80042-8

  日期：——

  Synthesis of pentanucleotide ApTpCpTpTp containing a 3′-terminal phosphomonoester group was accomplished with the help of the new phosphate-solid phase link 2-(4-carboxyphenyl-mercapto)ethanol; a similar molecule, 2-benzylsulfonylethanol, revealed interesting features as a temporary 3′-phosphate protecting group.

  借助新型的磷酸-固相键2-（4-羧基苯基-巯基）乙醇完成了含有3'-末端磷酸单酯基团的五核苷酸ApTpCpTpTp的合成。一个类似的分子2-苄基磺酰基乙醇，作为一个临时的3'-磷酸保护基显示出有趣的特征。
• 6-N-1 Trobenzotriazol-1-Yloxytris(Dimethylamino)Phosphonium Hexafluorophosphate (NBOP): A New Coupling Reagent in Oligonucleotide Synthesis
  作者：S. A. Nadeem Hashmi、M. Adiraj、Anil Kumar、S. B. Katti

  DOI：10.1080/15257779408011879

  日期：1994.6

  6-Nitrobenzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (NBOP, 2) has been demonstrated as an efficient coupling reagent in oligonucleotide synthesis. The reagent is stable and gives high coupling yields without any side products.
• TAKEDA, TADAYUKI;IKEDA, KAZUYOSHI;MIZUNO, YOSHIHISA;UEDA, TOHRU, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3558-3567
  作者：TAKEDA, TADAYUKI、IKEDA, KAZUYOSHI、MIZUNO, YOSHIHISA、UEDA, TOHRU

  DOI：——

  日期：——
• Phosphorus-31 NMR study of the mechanism of activation and coupling reactions in the synthesis of oligodeoxyribonucleotides by the phosphotriester method
  作者：Srinivasan Chandrasegaran、Akira Murakami、Lou Sing Kan

  DOI：10.1021/jo00199a039

  日期：1984.12