5'-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidine-3'-H-phosphonate | 110237-98-4

• 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'-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidine-3'-H-phosphonate
• 英文别名: [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxyphosphinic acid
• CAS: 110237-98-4
• 化学式: C₃₇H₃₆N₃O₉P
• 分子量: 697.681
• InChiKey: XGIQNHCZYGJMQF-VOTWKOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  147.44
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidine-3'-H-phosphonate 在 吡啶 、 碘 、 氯磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidin-3'-yl phosphate
  参考文献：
  名称：

  Cieslak; Jankowska; Sobkowski, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 1, p. 31 - 37

  摘要：

  DOI：
• 作为产物：
  描述：

  在 吡啶 、 水 作用下， 反应 1.0h， 生成 5'-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidine-3'-H-phosphonate
  参考文献：
  名称：

  芳基氢膦酸铵在制备核苷氢膦酸结构单元中的用途

  摘要：

  使用4-甲基苯基H-膦酸铵4c将5'- O-（二甲氧基三苯甲基）-2'-脱氧核苷衍生物6转化为相应的3'- H-膦酸酯2，并以高纯度分离得到。高产。

  DOI：

  10.1016/0040-4039(96)01993-4

文献信息

• 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。
• Solution-Phase Synthesis of Phosphorothioate Oligonucleotides Using a Solid-Supported Acyl Chloride withH-Phosphonate Chemistry
  作者：Ilaria Adamo、Cécile Dueymes、Andreas Schönberger、Aude-Emmanuelle Navarro、Albert Meyer、Meinolf Lange、Jean-Louis Imbach、Fritz Link、François Morvan、Jean-Jacques Vasseur

  DOI：10.1002/ejoc.200500547

  日期：2006.1

  The synthesis of oligonucleotides from dimers to a hexamer by a H-phosphonate approach in solution using solid-supported acyl chloride is reported herein. This strategy avoids the use of chromatography. The work-ups have been simplified and involve filtration, aqueous extraction and precipitation. The synthesis was scaled up to 1 mmol for the dimers and 340 μmol for the hexamer. (© Wiley-VCH Verlag

  本文报道了使用固体负载的酰氯在溶液中通过 H-膦酸酯方法将寡核苷酸从二聚体合成为六聚体。该策略避免使用色谱法。后处理已被简化，包括过滤、水萃取和沉淀。二聚体的合成放大到 1 mmol，六聚体的合成放大到 340 μmol。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach
  作者：Per J. Garegg、Ingvar Lindh、Tor Regberg、Jacek Stawinski、Roger Strömberg、Christina Henrichson

  DOI：10.1016/s0040-4039(00)84908-4

  日期：1986.1
• On the chemistry of RNA degradation by Fe·bleomycin
  作者：Chris E. Holmes、Robert J. Duff、Gijs A. van der Marel、Jacques van Boom、Sidney M. Hecht

  DOI：10.1016/s0968-0896(97)00038-2

  日期：1997.6

  The chemistry of RNA degradation by Fe bleomycin was studied using two RNA substrates that are modified efficiently at a small number of sites by the antitumor antibiotic. Cleavage of a tRNA(His) precursor transcript by Fe(II).BLM A(2) was shown to require O-2; cleavage was also observed when the same substrate was treated with Fe(III).BLM A(2) + H2O2. Consistent with earlier observations made for DNA, the extent of tRNA(His) precursor cleavage was greater for Fe(II).BLM A(5), than for Fe(II).BLM A(2); the least cleavage was obtained using Fe(II).BLM demethyl A(2). By the use of a P-32 end labeled tRNA precursor transcript that was also H-3 labeled within the uracil moieties, it was shown that release of uracil was nearly stoichiometric with tRNA strand scission by Fe(II).BLM A(2). Nonetheless, treatment of the tRNA(His) with hydrazine following BLM-mediated cleavage indicated formation of a new product that must have derived from a BLM-induced lesion. Also employed far characterization of BLM cleavage of RNA were the octanucleotides CGCTAGCG, C-3-ribo-CGCTAGCG and C-3-ara-CGCTAGCG. Analysis of the products of cleavage indicates that Fe . BLM is capable of mediating cleavage by abstraction of a H atom either from C-4'H or C-1'H of the chimeric oligonucleotides. (C) 1997 Elsevier Science Ltd.
• STAWINSKI, JACEK;THELIN, MATS, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 129-135
  作者：STAWINSKI, JACEK、THELIN, MATS

  DOI：——

  日期：——