(2R,3R,4R,5R)-2-((6aR,9R)-9-(acetoxymethyl)-7-methyl-6a,7,8,9-tetrahydroindolo[4,3-fg]quinolin-4(6H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate | 189143-78-0

• 分子结构分类: 有机化合物
• 英文名称: (2R,3R,4R,5R)-2-((6aR,9R)-9-(acetoxymethyl)-7-methyl-6a,7,8,9-tetrahydroindolo[4,3-fg]quinolin-4(6H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS: 189143-78-0
• 化学式: C₄₄H₄₀N₂O₉
• 分子量: 740.81
• InChiKey: FWQSXBUFWGZCLE-YOCCHQSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  55.0
• 可旋转键数：
  10.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  122.6
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-((6aR,9R)-9-(acetoxymethyl)-7-methyl-6a,7,8,9-tetrahydroindolo[4,3-fg]quinolin-4(6H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 以 甲醇 、 水 、 三乙胺 为溶剂， 反应 24.0h， 以79%的产率得到(2R,3S,4R,5R)-2-Hydroxymethyl-5-((6aR,9R)-9-hydroxymethyl-7-methyl-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of N-β-D-Ribosides of Ergot Alkaloids

  摘要：

  N-beta-D-Ribosides of agroclavine (1), elymoclavine (2), lysergene (4), lysergol (3), and 9,10-dihydrolysergol (5) were prepared by SnCl2 catalyzed ribosylation of their TMS derivatives with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. None of the new compounds exhibited activity against HIV or other viruses tested.

  DOI：

  10.1080/07328319708002525
• 作为产物：
  描述：

  O-Acetyl-lysergol 在 四氯化锡 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (2R,3R,4R,5R)-2-((6aR,9R)-9-(acetoxymethyl)-7-methyl-6a,7,8,9-tetrahydroindolo[4,3-fg]quinolin-4(6H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of N-β-D-Ribosides of Ergot Alkaloids

  摘要：

  N-beta-D-Ribosides of agroclavine (1), elymoclavine (2), lysergene (4), lysergol (3), and 9,10-dihydrolysergol (5) were prepared by SnCl2 catalyzed ribosylation of their TMS derivatives with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. None of the new compounds exhibited activity against HIV or other viruses tested.

  DOI：

  10.1080/07328319708002525