N4-acetyl-3’,5’-O-di-tert-silyl cytidine | 1245818-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N4-acetyl-3’,5’-O-di-tert-silyl cytidine
• 英文别名: N⁴-acetyl-3’,5’-O-di-tert-silyl cytidine；3',5'-O-di-tert-butylsilyl-N⁴-acetylcytidine
• CAS: 1245818-50-1
• 化学式: C₁₉H₃₁N₃O₆Si
• 分子量: 425.557
• InChiKey: IZFIMXDESWCRLO-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  111.91
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N4-acetyl-3’,5’-O-di-tert-silyl cytidine 在 吡啶 、 咪唑 、 1,3-二氯-5,5-二甲基海因 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.67h， 生成
  参考文献：
  名称：

  Chemical Synthesis of U1 snRNA Derivatives

  摘要：

  U1 snRNA is an interesting biological tool for splicing correction and regulation of gene expression. However, U1 snRNA has never been chemically synthesized. In this study, the first chemical synthesis of U1snRNA and its analogues was carried out. Moreover, it was found that the binding affinity of the modified U1 snRNA with an ethylene glycol linkage to snurportin 1 (nuclear import adaptor) was as high as that of the unmodified RNA.

  DOI：

  10.1021/ol401917r
• 作为产物：
  描述：

  3',5'-O-(Di-tert-butylsilanediyl)cytidine 、 乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到N4-acetyl-3’,5’-O-di-tert-silyl cytidine
  参考文献：
  名称：

  Chemical Synthesis of U1 snRNA Derivatives

  摘要：

  U1 snRNA is an interesting biological tool for splicing correction and regulation of gene expression. However, U1 snRNA has never been chemically synthesized. In this study, the first chemical synthesis of U1snRNA and its analogues was carried out. Moreover, it was found that the binding affinity of the modified U1 snRNA with an ethylene glycol linkage to snurportin 1 (nuclear import adaptor) was as high as that of the unmodified RNA.

  DOI：

  10.1021/ol401917r

文献信息

• The Spontaneous Rearrangement of 2,4-Dinitrophenyl Substituent in Ribonucleosides Under Neutral Conditions
  作者：Anna Olejnik、Zofia Gdaniec、Elzbieta Kierzek、Ryszard Kierzek

  DOI：10.1080/15257770.2010.507233

  日期：2010.8.13

  adenosine derivatives an isomerization of a 2,4-dinitrophenyl group between the 2′- and 3′-positions of the ribose was observed under neutral conditions. Moreover, it was shown that isomerization of the 2,4-dinitrophenyl group in conditions required to synthesize phosphoramidites and lability in aqueous ammonia make chemical synthesis of 2′-O-(2,4-dinitrophenyl) oligonucleotides impossible.

  在胞苷和腺苷衍生物中，在中性条件下观察到2，4-二硝基苯基在核糖的2'-和3'-位之间的异构化。此外，显示了在合成亚磷酰胺所需的条件下2，4-二硝基苯基的异构化和在氨水中的不稳定性使得2'-O-（2，4-二硝基苯基）寡核苷酸的化学合成成为不可能。
• 2′-O-{[2,2-dimethyl-2-(2-nitrophenyl) acetyl] oxy} methyl protecting group for RNA synthesis
  作者：Ke Chen、Wei Wang、Dezhong Qu、Haoting Zhao、Wei Xiong、Caijie Luo、Menghui Yin、Biliang Zhang

  DOI：10.1016/j.tetlet.2013.06.001

  日期：2013.8

  A new 2′-OH protecting group, [2,2-dimethyl-2-(2-nitrophenyl)acetyl]oxy} methyl (DAM), has been successfully applied to RNA oligonucleotides synthesis with high coupling efficiency. The 2′-O-DAM method is fully compatible with reagents and conditions employed in automated solid phase synthesis of RNA. Moreover, it can be easily removed via reduction in near-neutral solution.

  一种新的2'-OH保护基，[2,2-二甲基-2-（2-硝基苯基）乙酰基]氧基}甲基（DAM）已成功地用于RNA寡核苷酸的合成，具有很高的偶联效率。2'- O- DAM方法与RNA自动固相合成中使用的试剂和条件完全兼容。此外，可以通过减少接近中性的溶液轻松地将其除去。