N2-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine | 160107-22-2

• 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: N2-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy(oxido)phosphaniumyl]oxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 160107-22-2
• 化学式: C₃₈H₄₁N₆O₉P
• 分子量: 756.752
• InChiKey: GWBGAQOYBOXGRM-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N2-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine 在 咪唑 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以73%的产率得到N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷
  参考文献：
  名称：

  Facile methods to recycle nucleosides during solid phase synthesis of oligonucleotides

  摘要：

  Solid phase syntheses of oligonucleotides, using nucleoside phosphoramidites or methylphosphonamidites require a large excess of nucleoside monomers over the hydroxy functions of the growing oligonucleotide chain bound onto the solid phase. The outlined method allows to recover the excess nucleosides. All the protective groups on the sugar and the nucleobase of the monomers are maintained throughout the recycling process.

  DOI：

  10.1016/s0040-4039(00)76822-5
• 作为产物：
  描述：

  5'-O-dimethoxytrityl-N2-isobutyryl-2'-deoxyguanosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 在 三氟乙酸吡啶 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 生成 N2-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
  参考文献：
  名称：

  H-膦酸酯二聚体的溶液相合成支链DNA杂种

  摘要：

  描述了一种溶液相合成具有四面体或伪八面体几何形状的分支寡核苷酸的方法，该方法包括将被保护的二核苷磷酸酯的3'- H-膦酸酯与有机核心分子偶联。二聚体结构单元是通过不需要色谱纯化的合成方法生产的，并且在不到三天的实验室工作中即可产生高达44％的H-膦酸酯二聚体。总共准备了七个不同的分支杂种，包括序列（CG）4 TBA的新杂种，其中TBA代表四（对-羟基联苯）金刚烷，它通过添加MgCl 2从微摩尔水溶液组装成一种材料。

  DOI：

  10.1021/jo202508n

文献信息

• COMPOUNDS FOR TREATING BACTERIAL INFECTIONS
  申请人：Glaser Gad

  公开号：US20110086813A1

  公开（公告）日：2011-04-14

  The present invention relates to a novel class of guanine nucleotide analogs which inhibit RelA and Relseq synthetic activity and which possess anti-bacterial activity. The present invention also relates to pharmaceutical compositions that include such compounds, and to methods of use of such compounds or compositions for combating bacteria and treating bacterial infections.

  本发明涉及一类新型鸟嘌呤核苷酸类似物，其抑制RelA和Relseq的合成活性，并具有抗细菌活性。本发明还涉及包括这些化合物的药物组合物，以及利用这些化合物或组合物来对抗细菌和治疗细菌感染的方法。
• 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.
• Thioalkylation of nucleoside-H-phosphonates and its application to solid phase synthesis of oligonucleotides
  作者：Wolfgang K.-D. Brill

  DOI：10.1016/0040-4039(94)02380-t

  日期：1995.1

  A facile method for the thioalkylation of H-phosphonate diesters is presented. It can be used in the solid phase synthesis of oligonucleotides according to the H-phosphonate method.
• Facile methods to recycle nucleosides during solid phase synthesis of oligonucleotides
  作者：Wolfgang K.-D. Brill

  DOI：10.1016/s0040-4039(00)76822-5

  日期：1994.5

  Solid phase syntheses of oligonucleotides, using nucleoside phosphoramidites or methylphosphonamidites require a large excess of nucleoside monomers over the hydroxy functions of the growing oligonucleotide chain bound onto the solid phase. The outlined method allows to recover the excess nucleosides. All the protective groups on the sugar and the nucleobase of the monomers are maintained throughout the recycling process.
• Solution-Phase Synthesis of Branched DNA Hybrids via <i>H</i>-Phosphonate Dimers
  作者：Arunoday Singh、Mariyan Tolev、Christine I. Schilling、Stefan Bräse、Helmut Griesser、Clemens Richert

  DOI：10.1021/jo202508n

  日期：2012.3.16

  method for the solution-phase synthesis of branched oligonucleotides with tetrahedral or pseudo-octahedral geometry is described that involves the coupling of 3′-H-phosphonates of protected dinucleoside phosphates and organic core molecules. The dimer building blocks are produced by a synthesis that requires no chromatographic purification and that produces the dimer H-phosphonates in up to 44% yield

  描述了一种溶液相合成具有四面体或伪八面体几何形状的分支寡核苷酸的方法，该方法包括将被保护的二核苷磷酸酯的3'- H-膦酸酯与有机核心分子偶联。二聚体结构单元是通过不需要色谱纯化的合成方法生产的，并且在不到三天的实验室工作中即可产生高达44％的H-膦酸酯二聚体。总共准备了七个不同的分支杂种，包括序列（CG）4 TBA的新杂种，其中TBA代表四（对-羟基联苯）金刚烷，它通过添加MgCl 2从微摩尔水溶液组装成一种材料。