5'-O-(4,4'-dimethoxytrityl)N-benzoyl-cytosine-3'-O-(2-cyanoethyl) H-phosphonate | 152998-05-5

• 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-(4,4'-dimethoxytrityl)N-benzoyl-cytosine-3'-O-(2-cyanoethyl) H-phosphonate
• 英文别名: N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate)；N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy(oxido)phosphaniumyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 152998-05-5
• 化学式: C₄₀H₃₉N₄O₉P
• 分子量: 750.745
• InChiKey: VZBRHWXMWMIHIF-UQDPWRLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)N-benzoyl-cytosine-3'-O-(2-cyanoethyl) H-phosphonate 在 咪唑 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以95%的产率得到N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷
  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-(4,4’-二甲氧基三苯基)-N4-苯甲酰基-2’-脱氧胞苷-3’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 三氟乙酸吡啶 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 生成 5'-O-(4,4'-dimethoxytrityl)N-benzoyl-cytosine-3'-O-(2-cyanoethyl) H-phosphonate
  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

• On the Compatibility of Azides in Phosphoramidite-Based Couplings: Synthesis of a Novel, Convertible Azido-Functionalized CyPLOS Analogue
  作者：Cinzia Coppola、Luca Simeone、Lorenzo De Napoli、Daniela Montesarchio

  DOI：10.1002/ejoc.201001057

  日期：2011.2

  transporters based on a CyPLOS (cyclic phosphate-linked oligosaccharide) backbone, we describe the synthesis of a novel azido-derivatized CyPLOS analogue that is tailored for practical post-synthetic functionalization with a variety of labels. As a prerequisite for the effective preparation of this phosphate-linked macrocycle, the compatibility of azido alcohols as coupling agents in phosphoramidite

  为了制备基于 CyPLOS（环状磷酸连接寡糖）骨架的离子转运蛋白库，我们描述了一种新型叠氮衍生的 CyPLOS 类似物的合成，该类似物专为具有各种标签的实际合成后功能化而量身定制。作为有效制备这种磷酸盐连接的大环的先决条件，通过使用 31 P NMR 光谱监测核苷 3'-亚磷酰胺与合适的标准偶联剂，在溶液中初步研究了叠氮醇作为亚磷酰胺合成方案中偶联剂的相容性。模型醇和叠氮化物。
• Stereospecific Protodeauration/Transmetalation Generating Configurationally Stable P‐Metalated Nucleoside Derivatives
  作者：Marcia E. Richard、Rosa M. Ciccarelli、Kevin J. Garcia、Erica J. Miller、Stephanie L. Casino、Robert. D. Pike、Robert A. Stockland Jr

  DOI：10.1002/ejoc.201800397

  日期：2018.5.24

  A stereospecific protodeauration/transmetalation sequence facilitated the synthesis of configurationally stable P‐metalated species. Mechanistic studies using model systems revealed the overall process to occur with retention of stereochemistry. This methodology was adapted for the synthesis of chiral P‐arylated nucleoside derivatives.

  立体有规的原金属去金属化/过渡金属化序列促进了构型稳定的P金属化物质的合成。使用模型系统进行的机理研究揭示了保留立体化学的整个过程。该方法适用于手性P-芳基化核苷衍生物的合成。
• SOLID PHASE OLIGONUCLEOTIDE SYNTHESIS BY USING β-CE<i>H</i>-PHOSPHONATE APPROACH
  作者：Kamlesh J. Padiya、Nikhil U. Mohe、Manikrao M. Salunkhe

  DOI：10.1081/scc-120002704

  日期：2002.1.1

  ABSTRACT A new approach to the solid phase synthesis of oligonucleotide is described, which is based on oxidative coupling of nucleoside 3′-β-CE H-phosphonates in presence of N-Bromosuccinimide (NBS) as a coupling agent.

  摘要描述了一种寡核苷酸固相合成的新方法，该方法基于在 N-溴代琥珀酰亚胺 (NBS) 作为偶联剂存在下核苷 3'-β-CE H-膦酸酯的氧化偶联。
• Commercially Available 5‘-DMT Phosphoramidites as Reagents for the Synthesis of Vinylphosphonate-Linked Oligonucleic Acids
  作者：Sahar Abbas、Richard D. Bertram、Christopher J. Hayes

  DOI：10.1021/ol0166045

  日期：2001.10.1

  [GRAPHICS]Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers T*T, d(C)*T, d(A)*T, and d(G)*T in modest to good yields. The T*T dimer was further elaborated to give a 5'-DMT-T*T-3'-CEP building block, and this was used in the automated synthesis of the TpT*TpT tetramer.
• 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.