1-azidopropyl 3,4,6,-tri-O-[(,2'3',4',6'-tetra-O-acetyl-β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside | 1393736-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-azidopropyl 3,4,6,-tri-O-[(,2'3',4',6'-tetra-O-acetyl-β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-6-(3-azidopropoxy)-3,4-bis[[1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazol-4-yl]methoxy]oxan-2-yl]methoxymethyl]triazol-1-yl]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 1393736-35-0
• 化学式: C₆₂H₈₃N₁₃O₃₃
• 分子量: 1538.41
• InChiKey: ZAWNPFYYMMXIGC-IMLXYCHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  108
• 可旋转键数：
  46
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  525
• 氢给体数：
  1
• 氢受体数：
  41

反应信息

• 作为反应物：
  描述：

  1-azidopropyl 3,4,6,-tri-O-[(,2'3',4',6'-tetra-O-acetyl-β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到1-azidopropyl 3,4,6,-tri-O-[(β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry

  摘要：

  The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GIcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GIcNAc-centered neoglycoclusters were assembled by reaction of a GIcNAc core containing peripheral propargyl funclionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.

  DOI：

  10.1021/jo3013435
• 作为产物：
  描述：

  p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium azide 作用下， 以 二氯甲烷 、 水 、 叔丁醇 、 乙腈 为溶剂， 反应 0.25h， 以0.25 g的产率得到1-azidopropyl 3,4,6,-tri-O-[(,2'3',4',6'-tetra-O-acetyl-β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry

  摘要：

  The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GIcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GIcNAc-centered neoglycoclusters were assembled by reaction of a GIcNAc core containing peripheral propargyl funclionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.

  DOI：

  10.1021/jo3013435