5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-β-cyanoethyl phosphorothioate | 224298-18-4

• 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: 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-β-cyanoethyl phosphorothioate
• 英文别名: 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-[5'-O-(dimethoxytrityl)thymidine] O-β-cyanoethyl phosphorothioate；N-[9-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]purin-6-yl]benzamide
• CAS: 224298-18-4
• 化学式: C₅₁H₅₁N₈O₁₂PS
• 分子量: 1031.05
• InChiKey: WRYMQWQJBZENDR-HQCOQJBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  73
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  272
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  保护胸苷 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 sulfur 、 一水合肼 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 、 溶剂黄146 为溶剂， 反应 3.67h， 生成 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-β-cyanoethyl phosphorothioate
  参考文献：
  名称：

  Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis

  摘要：

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.

  DOI：

  10.1080/15257770008033035

文献信息

• Site-specific labeling of DNA sequences containing phosphorothioate diesters
  作者：Jacqueline A. Fidanza、Hiroaki Ozaki、Larry W. McLaughlin

  DOI：10.1021/ja00040a004

  日期：1992.7

  A phosphorothioate diester can be incorporated site-specifically into DNA sequences to provide a nucleophilic site that is amenable to alkylation by labels containing haloacetamide, aziridine sulfonamide, or γ-bromo-α,β-unsaturated carbonyl functionalities. Labeling reactions proceed most efficiently at 50 o C in the pH range 5.0-8.0 and require a number of hours for completion. HPLC techniques employing

  硫代磷酸二酯可以位点特异性地掺入 DNA 序列中，以提供一个亲核位点，该位点可通过含有卤代乙酰胺、氮丙啶磺酰胺或 γ-溴-α,β-不饱和羰基官能团的标记进行烷基化。标记反应在 50 o C 在 5.0-8.0 的 pH 值范围内最有效地进行，并且需要数小时才能完成。采用反相柱的 HPLC 技术可用于快速纯化标记材料，并显示了各种示例，包括位点特异性标记的 30 聚体的纯化
• Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis
  作者：Takanori Miyashita、Kohei Yamada、Kazuhiko Kondo、Kenya Mori、Kazuo Shinozuka

  DOI：10.1080/15257770008033035

  日期：2000.5

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.