methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate | 153751-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate
• CAS: 153751-21-4
• 化学式: C₃₇H₂₉NO₉
• 分子量: 631.639
• InChiKey: GSOQJPAJEFIGCP-LVVLYVGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  127.32
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate 在 ammonium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 197.0h， 生成 4-(2,3-O-isopropylidene-β-D-ribofuranosyl)quinoline-2-carboxamide
  参考文献：
  名称：

  C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(b-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

  摘要：

  Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)furan-2(5 ($) under bar H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-($) under bar O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide ($) under bar C-nucleoside (7).

  DOI：

  10.3987/com-93-6524
• 作为产物：
  描述：

  5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate
  参考文献：
  名称：

  C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(b-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

  摘要：

  Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)furan-2(5 ($) under bar H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-($) under bar O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide ($) under bar C-nucleoside (7).

  DOI：

  10.3987/com-93-6524