[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate | 656249-32-0

• 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: [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate
• CAS: 656249-32-0
• 化学式: C₅₇H₆₄N₁₁O₁₅P
• 分子量: 1174.17
• InChiKey: ZDKADKHMHIMJEV-HBKBGLFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  84
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  318
• 氢给体数：
  4
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate 在 diethyldithiocarbonate disulfide 作用下， 反应 1.0h， 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)-[[(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-3-(4-oxopentanoyloxy)oxolan-2-yl]methoxy]-sulfidophosphanium
  参考文献：
  名称：

  Oligodeoxyribonucleotide Phosphorothioates: Substantial Reduction of (N-1)-mer Content Through the Use of Trimeric Phosphoramidite Synthons

  摘要：

  Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monomers. A 20-mer oligodeoxyribonucleotide phosphorothioate which is in phase I clinical trials was chosen as an example for the studies.

  DOI：

  10.1080/15257779908043091
• 作为产物：
  描述：

  N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 在 四氮唑 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate
  参考文献：
  名称：

  Oligodeoxyribonucleotide Phosphorothioates: Substantial Reduction of (N-1)-mer Content Through the Use of Trimeric Phosphoramidite Synthons

  摘要：

  Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monomers. A 20-mer oligodeoxyribonucleotide phosphorothioate which is in phase I clinical trials was chosen as an example for the studies.

  DOI：

  10.1080/15257779908043091

文献信息

• High-Yield Solution-Phase Synthesis of Di- and Trinucleotide Blocks Assisted by Polymer-Supported Reagents
  作者：Cécile Dueymes、Andreas Schönberger、Ilaria Adamo、Aude-Emmanuelle Navarro、Albert Meyer、Meinolf Lange、Jean-Louis Imbach、Fritz Link、François Morvan、Jean-Jacques Vasseur

  DOI：10.1021/ol0511777

  日期：2005.8.1

  [GRAPHICS]A new solution-phase phosphoramidite approach is reported for oligonucleotide synthesis employing recyclable solid-supported reagents. It uses polyvinyl pyridinium tosylate as the activator of a nucleoside-3'-O-phosphoramidite in the coupling step with a 5'-OH nucleoside or dinucleotide. The resulting phosphite triester was either sulfurized or oxidized using polystyrene-bound trimethylammonium tetrathionate or periodiate. This method avoids complicated purification steps, as excess reagents are easily removed by filtration.
• Oligodeoxyribonucleotide Phosphorothioates: Substantial Reduction of (N-1)-mer Content Through the Use of Trimeric Phosphoramidite Synthons
  作者：Alessandra Eleuteri、Daniel C. Capaldi、Douglas L. Cole、Vasulinga T. Ravikumar

  DOI：10.1080/15257779908043091

  日期：1999.3

  Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monomers. A 20-mer oligodeoxyribonucleotide phosphorothioate which is in phase I clinical trials was chosen as an example for the studies.