N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-di-tert-butylsilanediylguanosine | 1207451-99-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-di-tert-butylsilanediylguanosine
• CAS: 1207451-99-7
• 化学式: C₃₆H₅₆N₆O₇SSi
• 分子量: 745.028
• InChiKey: JFGNDPSDELYGJW-QBVBFOPXSA-N

物化性质

• 沸点：
  813.8±75.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150.49
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-di-tert-butylsilanediylguanosine 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以84%的产率得到N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-O-methyl-3',5'-O-di-tert-butylsilanediylguanosine
  参考文献：
  名称：

  Facile and efficient approach for the synthesis of N2-dimethylaminomethylene-2′-O-methylguanosine

  摘要：

  A convenient method for the synthesis of N-2-dimethylaminomethylene-2'-O-methylguanosine (1), which is a useful intermediate for oligonucleotide construction, was developed. We chose the di-tert-butylsilyl group and the triisopropylbenzenesulfonyl group as sugar and base protecting groups, respectively. These protecting groups were stable during the 2'-O-methylation step with MeI and NaH. Our six-step synthesis of 1 is easy to perform using commercially available reagents, and requires only three chromatographic purifications. Compound 1 was obtained in 56% yield from guanosine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.016
• 作为产物：
  描述：

  O⁶-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-(di-tert-butylsilanediyl)guanosine 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-di-tert-butylsilanediylguanosine
  参考文献：
  名称：

  Facile and efficient approach for the synthesis of N2-dimethylaminomethylene-2′-O-methylguanosine

  摘要：

  A convenient method for the synthesis of N-2-dimethylaminomethylene-2'-O-methylguanosine (1), which is a useful intermediate for oligonucleotide construction, was developed. We chose the di-tert-butylsilyl group and the triisopropylbenzenesulfonyl group as sugar and base protecting groups, respectively. These protecting groups were stable during the 2'-O-methylation step with MeI and NaH. Our six-step synthesis of 1 is easy to perform using commercially available reagents, and requires only three chromatographic purifications. Compound 1 was obtained in 56% yield from guanosine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.016