6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine | 863591-95-1

• 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: 6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine
• CAS: 863591-95-1
• 化学式: C₂₉H₃₉N₅O₉SSi
• 分子量: 661.808
• InChiKey: ACJAQTMRVJBVBC-ZYWWQZICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  169.11
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine 以 甲醇 为溶剂， 反应 1.5h， 以85%的产率得到5'-O-(tert-butyldimethylsilyl)-2'-O-(p-tolylsulfonyl)adenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w
• 作为产物：
  描述：

  乙酸酐 、 5'-O-(tert-butyldimethylsilyl)-2'-O-(p-tolylsulfonyl)adenosine 在 吡啶 作用下， 生成 Acetic acid (2R,3R,4R,5R)-5-(6-acetylamino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester 、 6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w