{[(N6-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester | 918334-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {[(N6-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester
• 英文别名: {[(N⁶-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester
• CAS: 918334-49-3
• 化学式: C₂₆H₂₆N₆O₅
• 分子量: 502.53
• InChiKey: SYMAAUNMZUJATM-UHFFFAOYSA-N

物化性质

• 沸点：
  728.3±70.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  128.54
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  {[(N6-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 35.5h， 生成 (S)-2-(2-{[((S)-1,2-Bis-tert-butoxycarbonyl-ethylcarbamoyl)-methyl]-[2-(6-methylamino-purin-9-yl)-acetyl]-amino}-acetylamino)-succinic acid di-tert-butyl ester
  参考文献：
  名称：

  Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase

  摘要：

  Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.

  DOI：

  10.1080/15257770500446857
• 作为产物：
  描述：

  dibenzyl iminodiacetate 在 叔丁基亚氨基-三(二甲氨基)正膦 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 {[(N6-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester
  参考文献：
  名称：

  Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase

  摘要：

  Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.

  DOI：

  10.1080/15257770500446857