1-(4,4'-dimethoxytrityloxy)-29-[N-(1-benzyloxycarbonylamino)butyl]carbamoylmethylenoxy-3,6,9,12,15,18,21,24,27-nonaoxanonacosane | 860030-85-9

• 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: 1-(4,4'-dimethoxytrityloxy)-29-[N-(1-benzyloxycarbonylamino)butyl]carbamoylmethylenoxy-3,6,9,12,15,18,21,24,27-nonaoxanonacosane
• CAS: 860030-85-9
• 化学式: C₅₅H₇₈N₂O₁₆
• 分子量: 1023.23
• InChiKey: VSSNCVZVTHZZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  73.0
• 可旋转键数：
  45.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  187.42
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  1-(4,4'-dimethoxytrityloxy)-29-[N-(1-benzyloxycarbonylamino)butyl]carbamoylmethylenoxy-3,6,9,12,15,18,21,24,27-nonaoxanonacosane 在 三氯乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以93%的产率得到29-[N-(1-benzyloxycarbonylamino)butyl]carbamoylmethylenoxy-3,6,9,12,15,18,21,24,27-nonaoxanonacosan-1-ol
  参考文献：
  名称：

  Efficient Preparation of Organic Substrate−RNA Conjugates via in Vitro Transcription

  摘要：

  A concise synthetic way has been developed for the preparation of guanosine monophosphate derivatives carrying a decaethylene glycol spacer at their 5'-oxygen to which are attached a range of organic substrates. The four different compounds, prepared via a convergent synthetic strategy, carry a tethered benzylallyl ether residue (1a), an anthracene (1b), a benzyl carbamate residue (1c), or a primary amino group (1d), respectively. All four compounds have been successfully incorporated at the T-end of a 25-mer long RNA transcript via T7 RNA polymerase, and no inhibition of chain elongation could be observed. Under proper conditions, 1a and 1b can be incorporated up to 90-95% and 1c up to 68%. The amino-terminated initiator Id is incorporated less efficiently although still up to 49%. These results show that the more hydrophobic the guanosine monophosphate derivative is, the higher is its enzymatic incorporation.

  DOI：

  10.1021/ja051179m
• 作为产物：
  描述：

  (4,4'-dimethoxytrityl)tetrakis(ethylene glycol) p-toluenesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 1-(4,4'-dimethoxytrityloxy)-29-[N-(1-benzyloxycarbonylamino)butyl]carbamoylmethylenoxy-3,6,9,12,15,18,21,24,27-nonaoxanonacosane
  参考文献：
  名称：

  Efficient Preparation of Organic Substrate−RNA Conjugates via in Vitro Transcription

  摘要：

  A concise synthetic way has been developed for the preparation of guanosine monophosphate derivatives carrying a decaethylene glycol spacer at their 5'-oxygen to which are attached a range of organic substrates. The four different compounds, prepared via a convergent synthetic strategy, carry a tethered benzylallyl ether residue (1a), an anthracene (1b), a benzyl carbamate residue (1c), or a primary amino group (1d), respectively. All four compounds have been successfully incorporated at the T-end of a 25-mer long RNA transcript via T7 RNA polymerase, and no inhibition of chain elongation could be observed. Under proper conditions, 1a and 1b can be incorporated up to 90-95% and 1c up to 68%. The amino-terminated initiator Id is incorporated less efficiently although still up to 49%. These results show that the more hydrophobic the guanosine monophosphate derivative is, the higher is its enzymatic incorporation.

  DOI：

  10.1021/ja051179m