p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside | 1393736-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-(4-methylphenyl)sulfanyl-4,5-bis(prop-2-ynoxy)-6-(prop-2-ynoxymethyl)oxan-3-yl]acetamide
• CAS: 1393736-31-6
• 化学式: C₂₄H₂₇NO₅S
• 分子量: 441.548
• InChiKey: HZUYZTUWQPREGJ-RMRNXIRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside 、 toluene-4-sulfonic acid 3-hydroxy-propyl ester 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 反应 0.03h， 以58%的产率得到p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside
  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：

  1,3,4,6-tetra-O-propargyl-2-acetamido-2-deoxy-D-glucopyranose 、 4-甲苯硫酚 以 二氯甲烷 为溶剂， 反应 16.0h， 以71%的产率得到p-tolyl 3,4,6-tri-O-propargyl-2-acetamido-2-deoxy-β-D-1-thioglucopyranoside
  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.