5'-O-(4,4'-Dimethoxytrityl)-2-N-((dimethylamino)methylene)-3'-deoxyguanosine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

• 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)-2-N-((dimethylamino)methylene)-3'-deoxyguanosine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• 英文别名: (2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2-(2-(((E)-(dimethylamino)methylene)amino)-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite；N'-[9-[(2R,3R,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• 化学式: C₄₃H₅₃N₈O₇P
• 分子量: 824.917
• InChiKey: SEYDEJSCFSWWFE-YFFXOFBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  59
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4R)-2-(hydroxymethyl)-4-pyrimidin-4-yloxy-cyclopentoxy]phosphinic acid 、 5'-O-(4,4'-Dimethoxytrityl)-2-N-((dimethylamino)methylene)-3'-deoxyguanosine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 在 5-(乙硫基)-1H-四唑 、 DDTT 、 水 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 2.42h， 生成
  参考文献：
  名称：

  Identification of Novel Carbocyclic Pyrimidine Cyclic Dinucleotide STING Agonists for Antitumor Immunotherapy Using Systemic Intravenous Route

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00374
• 作为产物：
  描述：

  鸟苷 在 吡啶 、 咪唑 、 偶氮二异丁腈 、 二异丙基铵盐四氮唑 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 266.0h， 生成 5'-O-(4,4'-Dimethoxytrityl)-2-N-((dimethylamino)methylene)-3'-deoxyguanosine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages

  摘要：

  Convenient, preparative scale synthetic routes to 2'-O-(beta-cyanoethyl N,N-diisopropylphosphoramidites) of 3'-deoxycytidine (1) and 3'-deoxyguanosine (2) are described. The 3'-deoxycytidine nucleoside 5 was constructed by a modified Hilbert-Johnson reaction in which N-(4-isobutyryl)-cytosine (4) was ribosylated with anomeric acetate 3. Nucleoside 5 was converted to 5'-O(dimethoxytrityl)-4-N-isobutyryl-3'-deoxycytidine (7) and phosphitylated to provide phosphoramidite 1. Access to derivatives of 3'-deoxyguanosine was provided by selective removal of the 3'-hydroxyl of guanosine (10). Thus, the 3'-O-thiocarbamate of 5'-O-(dimethoxytrityl)-2-N-(dimethylformamidyl)- 2'-O-(triisopropylsilyl)guanosine (12) was reduced with tributyltin hydride and converted to phosphoramidite 2. In results to be reported elsewhere, phosphoramidites 1 and 2 were used to prepare oligodeoxynucleotides containing novel 2',5'-phosphodiester linkages using automated solid-phase DNA synthesis methods with average stepwise coupling yields of >97%.

  DOI：

  10.1021/jo00103a014