phenyl 2-(4-azidobutyryl)-3-O-acetyl-1-thio-β-D-glucopyranoside | 220971-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-(4-azidobutyryl)-3-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-4-acetyloxy-5-hydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl] 4-azidobutanoate
• CAS: 220971-79-9
• 化学式: C₁₈H₂₃N₃O₇S
• 分子量: 425.463
• InChiKey: KOSBAVGKRNFYDT-LHKMKVQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2-(4-azidobutyryl)-3-O-acetyl-1-thio-β-D-glucopyranoside 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 phenyl 2-(4-azidobutyryl)-3,4,6-tri-O-acetyl-1-sulfinyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Vancomycin from the Aglycon

  摘要：

  Vancomycin-resistant bacterial strains pose a serious threat to human health. Efforts to overcome vancomycin resistance by modifying the natural product have shown that the carbohydrates help modulate biological activity. To explore the mechanisms by which the carbohydrates function, it would be useful to have access to vancomycin derivatives containing different disaccharides. We now describe the synthesis of vancomycin from a readily available protected aglycon. This chemistry lays the groundwork for wide-ranging investigations of the roles of the carbohydrates in the biological activity of vancomycin. Moreover, in developing methods to glycosylate vancomcyin, we have extended the utility of the sulfoxide glycosylation reaction considerably by making it possible to use unhindered esters as neighboring groups. The chemistry we describe may also have implications for how to improve some other glycosylation methods.

  DOI：

  10.1021/ja983504u
• 作为产物：
  描述：

  4-azidobutanoyl chloride 、 苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 、 乙酰氯 在 吡啶 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 生成 、 phenyl 2-(4-azidobutyryl)-3-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Vancomycin from the Aglycon

  摘要：

  Vancomycin-resistant bacterial strains pose a serious threat to human health. Efforts to overcome vancomycin resistance by modifying the natural product have shown that the carbohydrates help modulate biological activity. To explore the mechanisms by which the carbohydrates function, it would be useful to have access to vancomycin derivatives containing different disaccharides. We now describe the synthesis of vancomycin from a readily available protected aglycon. This chemistry lays the groundwork for wide-ranging investigations of the roles of the carbohydrates in the biological activity of vancomycin. Moreover, in developing methods to glycosylate vancomcyin, we have extended the utility of the sulfoxide glycosylation reaction considerably by making it possible to use unhindered esters as neighboring groups. The chemistry we describe may also have implications for how to improve some other glycosylation methods.

  DOI：

  10.1021/ja983504u