4-ethynylbenzyl β-D-glucopyranoside | 1261138-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethynylbenzyl β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[(4-ethynylphenyl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1261138-95-7
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: VIPJIIWERYKYDB-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 4-ethynylbenzyl β-D-glucopyranoside 在 安息香双甲醚 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[(Z)-2-[4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]phenyl]ethenyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid 、 (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[(E)-2-[4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]phenyl]ethenyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  An Insight into the Radical Thiol/Yne Coupling: The Emergence of Arylalkyne-Tagged Sugars for the Direct Photoinduced Glycosylation of Cysteine-Containing Peptides

  摘要：

  An explorative study of the Thiol-Yne Coupling (TYC) reaction has been carried out using an aliphatic (1-octyne) and an aromatic alkyne (phenylacetylene) and two alkanethiols (methyl thioglycolate and N-acetyl-L-cysteine methyl ester). The outcomes of the TYC reactions strongly depend on the experimental conditions (e.g., temperature, solvent, and alkyne/thiol ratio), but these can be properly adjusted to achieve selective production of either mono- or bis-coupling products. With respect to 1-octyne, phenylacetylene undergoes notably easier radical hydrothiolation, further showing a notably higher aptitude for monohydrothiolation exclusive of bis-hydrothiolation. The overall findings were exploited in glycosylation of cysteine derivatives as well as of cysteine-containing peptides. A sugar featuring an arylacetylene moiety gave rise to a true click-reaction, that is, glycosylation of the tripeptide glutathione in its native form, by means of virtually equimolar amounts of reagents. This reaction was successfully applied, under physiological conditions, to a cysteine-containing nonapeptide with marked advantages over the analogous Thiol-Ene Coupling (TEC) derivatization. A TYC/TEC sequence affording bis-armed cysteine derivatives through dual functionalization of an alkynyl sugar was additionally devised.

  DOI：

  10.1021/jo101906j
• 作为产物：
  描述：

  4-乙基苄醇 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 4-ethynylbenzyl β-D-glucopyranoside
  参考文献：
  名称：

  An Insight into the Radical Thiol/Yne Coupling: The Emergence of Arylalkyne-Tagged Sugars for the Direct Photoinduced Glycosylation of Cysteine-Containing Peptides

  摘要：

  An explorative study of the Thiol-Yne Coupling (TYC) reaction has been carried out using an aliphatic (1-octyne) and an aromatic alkyne (phenylacetylene) and two alkanethiols (methyl thioglycolate and N-acetyl-L-cysteine methyl ester). The outcomes of the TYC reactions strongly depend on the experimental conditions (e.g., temperature, solvent, and alkyne/thiol ratio), but these can be properly adjusted to achieve selective production of either mono- or bis-coupling products. With respect to 1-octyne, phenylacetylene undergoes notably easier radical hydrothiolation, further showing a notably higher aptitude for monohydrothiolation exclusive of bis-hydrothiolation. The overall findings were exploited in glycosylation of cysteine derivatives as well as of cysteine-containing peptides. A sugar featuring an arylacetylene moiety gave rise to a true click-reaction, that is, glycosylation of the tripeptide glutathione in its native form, by means of virtually equimolar amounts of reagents. This reaction was successfully applied, under physiological conditions, to a cysteine-containing nonapeptide with marked advantages over the analogous Thiol-Ene Coupling (TEC) derivatization. A TYC/TEC sequence affording bis-armed cysteine derivatives through dual functionalization of an alkynyl sugar was additionally devised.

  DOI：

  10.1021/jo101906j