methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-β-D-glucopyranoside | 857351-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-5-amino-2-(azidomethyl)-4-benzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 857351-77-0
• 化学式: C₂₁H₂₂N₄O₆
• 分子量: 426.429
• InChiKey: FBPDDCWONSQPNA-PDOZGGDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-β-D-glucopyranoside 、 (S)-3-(4-Hydroxy-phenyl)-2-[(S)-3-(4-hydroxy-phenyl)-2-propynoylamino-propionylamino]-propionic acid 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以333 mg的产率得到[(2R,3R,4R,5R,6R)-2-(azidomethyl)-4-benzoyloxy-5-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-3-(4-hydroxyphenyl)-2-(prop-2-ynoylamino)propanoyl]amino]propanoyl]amino]-6-methoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  C₂-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles

  摘要：

  An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be Cul and N,N-diisopropylethylamine in CH3-CN.

  DOI：

  10.1021/jo050585l
• 作为产物：
  描述：

  methyl O-3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 在 18-冠醚-6 吡啶 、 三乙基硅烷 、 sodium azide 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-β-D-glucopyranoside
  参考文献：
  名称：

  C₂-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles

  摘要：

  An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be Cul and N,N-diisopropylethylamine in CH3-CN.

  DOI：

  10.1021/jo050585l

文献信息

• <i>C</i>₂-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles
  作者：Johan F. Billing、Ulf J. Nilsson

  DOI：10.1021/jo050585l

  日期：2005.6.1

  An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be Cul and N,N-diisopropylethylamine in CH3-CN.