5-amino-1-(2,3-O-isopropylidene-5-O-triphenylmethyl-β-D-ribofuranosyl)imidazole-4-carboxamide | 157762-07-7

• 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: 5-amino-1-(2,3-O-isopropylidene-5-O-triphenylmethyl-β-D-ribofuranosyl)imidazole-4-carboxamide
• 英文别名: methyl 2-[[1-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-aminoimidazole-4-carbonyl]amino]acetate
• CAS: 157762-07-7
• 化学式: C₃₄H₃₆N₄O₇
• 分子量: 612.682
• InChiKey: QSNUIUFEGMCLHO-FANUBLADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-amino-1-(2,3-O-isopropylidene-5-O-triphenylmethyl-β-D-ribofuranosyl)imidazole-4-carboxamide 在 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 4,5,7,8-Tetrahydro-6H-3-β-D-ribofuranosylimidazo<4,5-e><1,4>diazepine-5,8-dione
  参考文献：
  名称：

  Nucleosides and Nucleotides. 130. The Synthesis of Imidazo[4, 5-e][1, 4] Diazepine Nucleosides FromN¹-Substituted Inosines

  摘要：

  New synthetic methods for pyrimidine ring-expanded xanthosine, guanosine, and inosine analogues containing imidazo[4,5-e][1,4]diazepine nucleus are described. Treatment of N-1-substituted inosine derivatives 5, 12, 19 with aqueous NaOH gave 5-amino-4-(N-substituted carbamoyl)imidazole derivatives, followed by appropriate manipulations to cyclize these to constitute imidazo[4,5-e][1,4]diazepine nucleosides 11, 17, 22.

  DOI：

  10.1080/15257779408012169
• 作为产物：
  描述：

  2',3'-O-isopropylidene-5'-O-triphenylmethyl-1-<(ethoxycarbonyl)methyl>-inosine 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 5-amino-1-(2,3-O-isopropylidene-5-O-triphenylmethyl-β-D-ribofuranosyl)imidazole-4-carboxamide
  参考文献：
  名称：

  Nucleosides and Nucleotides. 130. The Synthesis of Imidazo[4, 5-e][1, 4] Diazepine Nucleosides FromN¹-Substituted Inosines

  摘要：

  New synthetic methods for pyrimidine ring-expanded xanthosine, guanosine, and inosine analogues containing imidazo[4,5-e][1,4]diazepine nucleus are described. Treatment of N-1-substituted inosine derivatives 5, 12, 19 with aqueous NaOH gave 5-amino-4-(N-substituted carbamoyl)imidazole derivatives, followed by appropriate manipulations to cyclize these to constitute imidazo[4,5-e][1,4]diazepine nucleosides 11, 17, 22.

  DOI：

  10.1080/15257779408012169

文献信息

• Nucleosides and Nucleotides. 130. The Synthesis of Imidazo[4, 5-<i>e</i>][1, 4] Diazepine Nucleosides From<i>N</i>¹-Substituted Inosines
  作者：Mitsutoshi Aoyagi、Noriaki Minakawa、Akira Matsuda

  DOI：10.1080/15257779408012169

  日期：1994.7

  New synthetic methods for pyrimidine ring-expanded xanthosine, guanosine, and inosine analogues containing imidazo[4,5-e][1,4]diazepine nucleus are described. Treatment of N-1-substituted inosine derivatives 5, 12, 19 with aqueous NaOH gave 5-amino-4-(N-substituted carbamoyl)imidazole derivatives, followed by appropriate manipulations to cyclize these to constitute imidazo[4,5-e][1,4]diazepine nucleosides 11, 17, 22.