methyl 6-azido-3,4-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2,6-dideoxy-β-D-glucopyranoside | 857351-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-3,4-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2,6-dideoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-2-(azidomethyl)-4-benzoyloxy-6-methoxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-3-yl] benzoate
• CAS: 857351-76-9
• 化学式: C₂₆H₃₀N₄O₈
• 分子量: 526.546
• InChiKey: JKAMFTPXXWGXMU-UNNUSUAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-3,4-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2,6-dideoxy-β-D-glucopyranoside 在 三乙基硅烷 、 1-羟基苯并三唑 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 [(2R,3R,4R,5R,6R)-5-[[(2S)-2-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(prop-2-ynoylamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-(azidomethyl)-4-benzoyloxy-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 、 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 methyl 6-azido-3,4-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-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.