| 1254708-43-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• CAS: 1254708-43-4
• 化学式: C₄₀H₅₆N₁₁O₁₄PSi
• 分子量: 974.009
• InChiKey: CGUNJWFBCYVCPF-OGZBXOCFSA-N

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl tetraisopropylphosphordiamidite 、 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 反应 21.5h， 以40%的产率得到
  参考文献：
  名称：

  Convenient Synthesis of a Propargylated Cyclic (3′-5′) Diguanylic Acid and Its “Click” Conjugation to a Biotinylated Azide

  摘要：

  The ribonucleoside building block, N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine, was prepared from commercial N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-propargyl guanosine in a yield of 91%. The propargylated guanylyl(3'-5')guanosine phosphotriester was synthesized from the reaction of N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine with N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-3'-O-[(2-cyanoethyl)-N, N-diisopropylaminophosphinyl] guanosine and isolated in a yield of 88% after P(III) oxidation, 3'-/5'-deprotection, and purification. The propargylated guanylyl(3'-5')guanosine phosphotriester was phosphitylated using 2-cyanoethyl tetraisopropylphosphordiamidite and 1H-tetrazole and was followed by an in situ intramolecular cyclization to give a propargylated c-di-GMP triester, which was isolated in a yield of 40% after P(III) oxidation and purification. Complete N-deacylation of the guanine bases and removal of the 2-cyanoethyl phosphate protecting groups from the propargylated c-di-GMP triester were performed by treatment with aqueous ammonia at ambient temperature. The final 2'-desilylation reaction was effected by exposure to triethylammonium trihydrofluoride affording the desired propargylated c-di-GMP diester, the purity of which exceeded 95%. Biotinylation of the propargylated c-di-GMP diester was easily accomplished through its cycloaddition reaction with a biotinylated azide derivative under click conditions to produce the biotinylated c-di-GMP conjugate of interest in an isolated yield of 62%.

  DOI：

  10.1021/bc1003857
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以2.25 g的产率得到
  参考文献：
  名称：

  Convenient Synthesis of a Propargylated Cyclic (3′-5′) Diguanylic Acid and Its “Click” Conjugation to a Biotinylated Azide

  摘要：

  The ribonucleoside building block, N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine, was prepared from commercial N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-propargyl guanosine in a yield of 91%. The propargylated guanylyl(3'-5')guanosine phosphotriester was synthesized from the reaction of N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine with N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-3'-O-[(2-cyanoethyl)-N, N-diisopropylaminophosphinyl] guanosine and isolated in a yield of 88% after P(III) oxidation, 3'-/5'-deprotection, and purification. The propargylated guanylyl(3'-5')guanosine phosphotriester was phosphitylated using 2-cyanoethyl tetraisopropylphosphordiamidite and 1H-tetrazole and was followed by an in situ intramolecular cyclization to give a propargylated c-di-GMP triester, which was isolated in a yield of 40% after P(III) oxidation and purification. Complete N-deacylation of the guanine bases and removal of the 2-cyanoethyl phosphate protecting groups from the propargylated c-di-GMP triester were performed by treatment with aqueous ammonia at ambient temperature. The final 2'-desilylation reaction was effected by exposure to triethylammonium trihydrofluoride affording the desired propargylated c-di-GMP diester, the purity of which exceeded 95%. Biotinylation of the propargylated c-di-GMP diester was easily accomplished through its cycloaddition reaction with a biotinylated azide derivative under click conditions to produce the biotinylated c-di-GMP conjugate of interest in an isolated yield of 62%.

  DOI：

  10.1021/bc1003857