[(2R,3S,5R)-2-[[[(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]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate | 187539-25-9

• 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-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate
• CAS: 187539-25-9
• 化学式: C₄₉H₅₄N₅O₁₅PS
• 分子量: 1016.03
• InChiKey: AJFNUEOGPBSIGJ-WRRDGYDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  71
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  272
• 氢给体数：
  2
• 氢受体数：
  17

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-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate 在 一水合肼 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 3-[[(2R,3S,5R)-2-[[[(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]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Improved Impurity Profile of Phosphorothioate Oligonucleotides Through the Use of Dimeric Phosphoramidite Synthons

  摘要：

  Phosphorothioate oligonucleotides synthesized through assembly of dimeric phosphoramidite synthons show a significantly improved impurity profile compared to oligomers synthesized through coupling of standard monomer phosphoramidites. A greater than 70% reduction of the (n-1)-mer population and a ca. 50% reduction of phosphodiester linkages has been achieved.

  DOI：

  10.1080/07328319708006244
• 作为产物：
  描述：

  保护胸苷 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 sulfur 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 3.5h， 生成 [(2R,3S,5R)-2-[[[(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]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate
  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

• Reactivity of 3H-1,2,4-dithiazole-3-thiones and 3H-1,2-dithiole-3-thiones as sulfurizing agents for oligonucleotide synthesis
  作者：Andrei P. Guzaev

  DOI：10.1016/j.tetlet.2010.11.086

  日期：2011.1

  The reactivity of 5-amino-3H-1,2,4-dithiazole-3-thiones substituted at their amino group and 5-amino-3H-1,2-dithiole-3-thiones substituted at their amino group and C4 toward compounds containing P(III) atoms has been studied. N,N-Disubstituted-N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)methanimidamides were selected as novel efficient sulfur transfer reagents suitable for DNA and RNA synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Improved Impurity Profile of Phosphorothioate Oligonucleotides Through the Use of Dimeric Phosphoramidite Synthons
  作者：Achim H. Krotz、Patrick Klopchin、Douglas L. Cole、Vasulinga T. Ravikumar

  DOI：10.1080/07328319708006244

  日期：1997.7

  Phosphorothioate oligonucleotides synthesized through assembly of dimeric phosphoramidite synthons show a significantly improved impurity profile compared to oligomers synthesized through coupling of standard monomer phosphoramidites. A greater than 70% reduction of the (n-1)-mer population and a ca. 50% reduction of phosphodiester linkages has been achieved.
• 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.
• Synthesis of Dimer Phosphoramidite Synthons for Oligodeoxyribonucleotide Phosphorothioates Using Diethyldithiocarbonate disulfide as an Efficient Sulfurizing Reagent
  作者：Alessandra Eleuteri、Zacharia S. Cheruvallath、Daniel C. Capaldi、Douglas L. Cole Vasulinga、T. Ravikumar

  DOI：10.1080/07328319908044844

  日期：1999.8

  An efficient solution phase synthesis of deoxyribonucleoside phosphorothioate dimers utilizing phosphoramidite approach is described. Diethyldithiocarbonate disulfide (DDD) was found to be an efficient sulfurizing reagent in the conversion of phosphite triesters to phosphorothioate triesters.