N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-O-methyl-3',5'-O-di-tert-butylsilanediylguanosine | 1207452-00-3

• 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)-2'-O-methyl-3',5'-O-di-tert-butylsilanediylguanosine
• CAS: 1207452-00-3
• 化学式: C₃₇H₅₈N₆O₇SSi
• 分子量: 759.055
• InChiKey: LBEXDUDDBZSMFJ-WIFIACMTSA-N

物化性质

• 沸点：
  777.8±70.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  52.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  139.49
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N2-dimethylaminomethylene-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-O-methyl-3',5'-O-di-tert-butylsilanediylguanosine 在 四甲基胍 、 2-硝基苯甲醛肟 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N'-[9-[(4aR,6R,7R,7aR)-2,2-ditert-butyl-7-methoxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
  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：

  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