tert-butyl 3-ethynyl-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-1H-indole-1-carboxylate | 1448664-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: tert-butyl 3-ethynyl-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-1H-indole-1-carboxylate
• CAS: 1448664-75-2
• 化学式: C₃₂H₄₃N₅O₇S
• 分子量: 641.789
• InChiKey: MWAQKRLDQCUGFX-MPYJOUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  149.02
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  D-阿拉伯糖 、 tert-butyl 3-ethynyl-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-1H-indole-1-carboxylate 、 二烯丙基胺 在 硼酸 、 异丙醇 、 三(五氟苯基)膦 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 生成 tert-butyl 3-((3S,4R,5S,6R)-3-(diallylamino)-4,5,6,7-tetrahydroxyhept-1-yn-1-yl)-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-1H-indole-1-carboxylate 、 tert-butyl 3-((3R,4R,5S,6R)-3-(diallylamino)-4,5,6,7-tetrahydroxyhept-1-yn-1-yl)-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-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
• 作为产物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 三乙胺 为溶剂， 反应 40.0h， 生成 tert-butyl 3-ethynyl-6-((2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamoyl)-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