1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-amino-4,6-O-benzylidene-β-D-glucopyranose | 1354639-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-amino-4,6-O-benzylidene-β-D-glucopyranose
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-7-amino-6-[4-(diphenylphosphanylmethyl)triazol-1-yl]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 1354639-07-8
• 化学式: C₂₈H₂₉N₄O₄P
• 分子量: 516.536
• InChiKey: VECJWAPEXDFYMN-BXZOIBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-amino-4,6-O-benzylidene-β-D-glucopyranose 、 2-二苯基膦苯甲醛 在 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-[o-(diphenylphosphino)benzylideneamino]-4,6-O-benzylidene-β-D-glucopyranose
  参考文献：
  名称：

  ‘ClickCarb’: modular sugar based ligands via click chemistry

  摘要：

  Reported is a modular approach for the synthesis of a number of structurally diverse ligands derived from carbohydrates. The use of the highly functional hydroxy amino azide 1 derived from glucosamine allows the synthesis of a number of useful ligands for organic and organometallic catalyses. The key step of the approach is the Huisgen cycloaddition of the anomeric sugar azide and diverse alkynes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.043
• 作为产物：
  描述：

  diphenylphosphineborane 在 三乙烯二胺 、 正丁基锂 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 0.5h， 生成 1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-amino-4,6-O-benzylidene-β-D-glucopyranose
  参考文献：
  名称：

  ‘ClickCarb’: modular sugar based ligands via click chemistry

  摘要：

  Reported is a modular approach for the synthesis of a number of structurally diverse ligands derived from carbohydrates. The use of the highly functional hydroxy amino azide 1 derived from glucosamine allows the synthesis of a number of useful ligands for organic and organometallic catalyses. The key step of the approach is the Huisgen cycloaddition of the anomeric sugar azide and diverse alkynes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.043
• 作为试剂：
  描述：

  1,3-二苯基-2-丙烯基乙酸酯 、 丙二酸二甲酯 在 N,O-双三甲硅基乙酰胺 、 bis(η3-allyl-μ-chloropalladium(II)) 、 1-[4-(diphenylphosphinomethyl)-1,2,3-triazol-1-yl]-1,2-dideoxy-2-amino-4,6-O-benzylidene-β-D-glucopyranose 、 potassium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到(E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate
  参考文献：
  名称：

  ‘ClickCarb’: modular sugar based ligands via click chemistry

  摘要：

  Reported is a modular approach for the synthesis of a number of structurally diverse ligands derived from carbohydrates. The use of the highly functional hydroxy amino azide 1 derived from glucosamine allows the synthesis of a number of useful ligands for organic and organometallic catalyses. The key step of the approach is the Huisgen cycloaddition of the anomeric sugar azide and diverse alkynes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.043

文献信息

• ‘ClickCarb’: modular sugar based ligands via click chemistry
  作者：Noureddine Khiar、Raquel Navas、Inmaculada Fernández

  DOI：10.1016/j.tetlet.2011.11.043

  日期：2012.1

  Reported is a modular approach for the synthesis of a number of structurally diverse ligands derived from carbohydrates. The use of the highly functional hydroxy amino azide 1 derived from glucosamine allows the synthesis of a number of useful ligands for organic and organometallic catalyses. The key step of the approach is the Huisgen cycloaddition of the anomeric sugar azide and diverse alkynes. (C) 2011 Elsevier Ltd. All rights reserved.