ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-α-D-glycero-pentofuranosyl)imidazole-1-carboxylate | 252054-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-α-D-glycero-pentofuranosyl)imidazole-1-carboxylate
• 英文别名: ethyl 4-[(2S,5S)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-2-yl]imidazole-1-carboxylate
• CAS: 252054-32-3
• 化学式: C₁₉H₁₉N₃O₅
• 分子量: 369.377
• InChiKey: PMBKSOSAQCQVBX-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  90.73
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-α-D-glycero-pentofuranosyl)imidazole-1-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以94%的产率得到5-[(trans-2,5)-5-aminomethyltetrahydrofuran-2-yl]imidazole
  参考文献：
  名称：

  Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹

  摘要：

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。

  DOI：

  10.1021/jo9910637
• 作为产物：
  描述：

  5-O-benzyl-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-D-threo-pentofuranose 在 palladium dihydroxide 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三乙基硼 、 偶氮二甲酸二异丙酯 、 三正丁基氢锡 、 环己烯 、 4-(二甲氨基)三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 22.75h， 生成 ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-α-D-glycero-pentofuranosyl)imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹

  摘要：

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。

  DOI：

  10.1021/jo9910637