tert-butyl 3-(((4R,5S)-2-oxo-5-((1R,2R,3R)-1,3,4-trihydroxy-2-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)oxazolidin-4-yl)ethynyl)-1H-indole-1-carboxylate | 1448665-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 3-(((4R,5S)-2-oxo-5-((1R,2R,3R)-1,3,4-trihydroxy-2-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)oxazolidin-4-yl)ethynyl)-1H-indole-1-carboxylate
• CAS: 1448665-22-2
• 化学式: C₂₈H₃₆N₂O₁₃
• 分子量: 608.599
• InChiKey: SAIAJABGDDHMHD-XBGNMDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  229.63
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(((4R,5S)-2-oxo-5-((1R,2R,3R)-1,3,4-trihydroxy-2-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)oxazolidin-4-yl)ethynyl)-1H-indole-1-carboxylate 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 3.0h， 以68%的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((1R,2R,3R)-1,3,4-triacetoxy-1-((4R,5S)-3-acetyl-4-((1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethynyl)-2-oxooxazolidin-5-yl)butan-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses

  摘要：

  A copper(I)-catalyzed anomeric aminoalkynylation reaction of unprotected aldoses was realized. Use of an electron-deficient phosphine ligand, boric acid to stabilize the iminium intermediate, and a protic additive (IPA) to presumably enhance reversible carbohydrate-boron complexation were all essential for efficient conversion. The reaction proceeded well even with a natural disaccharide substrate, suggesting that the developed catalytic reaction could be useful for the synthesis of glycoconjugates with minimum use of protecting groups.

  DOI：

  10.1021/ol401810b
• 作为产物：
  描述：

  tert-butyl 3-((3R,4S,5R,6R,7R)-3-(diallylamino)-4,5,7,8-tetrahydroxy-6-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)oct-1-yn-1-yl)-1H-indole-1-carboxylate 在 1,3-二甲基巴比妥酸 、 palladium diacetate 、 碳酸氢钠 、 对硝基苯基氯甲酸酯 、 三苯基膦 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 tert-butyl 3-(((4R,5S)-2-oxo-5-((1R,2R,3R)-1,3,4-trihydroxy-2-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)oxazolidin-4-yl)ethynyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses

  摘要：

  A copper(I)-catalyzed anomeric aminoalkynylation reaction of unprotected aldoses was realized. Use of an electron-deficient phosphine ligand, boric acid to stabilize the iminium intermediate, and a protic additive (IPA) to presumably enhance reversible carbohydrate-boron complexation were all essential for efficient conversion. The reaction proceeded well even with a natural disaccharide substrate, suggesting that the developed catalytic reaction could be useful for the synthesis of glycoconjugates with minimum use of protecting groups.

  DOI：

  10.1021/ol401810b