1,3,4,6-tetra-O-propargyl-2-acetamido-2-deoxy-β-D-glucopyranoside | 1393736-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-propargyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2,4,5-tris(prop-2-ynoxy)-6-(prop-2-ynoxymethyl)oxan-3-yl]acetamide
• CAS: 1393736-40-7
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: ANNIFTAIVZFYDR-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-GlcNAc 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 以50%的产率得到
  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

文献信息

• Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry
  作者：Dong Jun Lee、Sung-Hyun Yang、Geoffrey M. Williams、Margaret A. Brimble

  DOI：10.1021/jo3013435

  日期：2012.9.7

  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.