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 | 1448665-12-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• 英文别名: tert-butyl 3-[(3R,4S,5R,6R,7R)-3-[bis(prop-2-enyl)amino]-4,5,7,8-tetrahydroxy-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoct-1-ynyl]indole-1-carboxylate
• CAS: 1448665-12-0
• 化学式: C₃₃H₄₆N₂O₁₂
• 分子量: 662.734
• InChiKey: JTTJMKGMVMSCHX-XFQHOVJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  215
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  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 4-二甲氨基吡啶 、 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 吡啶 、 乙醇 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 (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：

  Lactose 、 3-乙炔基-1H-吲哚-1-羧酸叔丁酯 、 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 36.0h， 以1.5%的产率得到
  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

文献信息

• Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses
  作者：Yasuaki Kimura、Soichi Ito、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ol401810b

  日期：2013.8.16

  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.