N-alloc-O-PMB vancomycin aglycon allyl ester | 220971-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-alloc-O-PMB vancomycin aglycon allyl ester
• 英文别名: (2R)-N-[(1S,2R,18R,19R,22S,25R,28R,40S)-5,15-dichloro-2,18,20,23,26,32,35,37,42,44-decahydroxy-22-(2-hydroxy-2-iminoethyl)-48-[(4-methoxyphenyl)methoxy]-40-prop-2-enoxycarbonyl-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,20,23,26,29(45),30,32,34(39),35,37,41,43,46,49-icosaen-19-yl]-4-methyl-2-[methyl(prop-2-enoxycarbonyl)amino]pentanimidic acid
• CAS: 220971-89-1
• 化学式: C₆₈H₆₈Cl₂N₈O₂₀
• 分子量: 1388.24
• InChiKey: KVLAWLOSMQXBGY-WLLFXTIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  98
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  434
• 氢给体数：
  13
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 N-alloc-O-PMB vancomycin aglycon allyl ester 在 caesium carbonate 作用下， 生成 N-alloc-tri-O-allyl-O-PMB vancomycin aglycon allyl ester
  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：

  万古霉素糖苷配基 在 碳酸氢钠 、 potassium hydrogencarbonate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-alloc-O-PMB vancomycin aglycon allyl ester
  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

文献信息

• Synthesis of Vancomycin from the Aglycon
  作者：Christopher Thompson、Min Ge、Daniel Kahne

  DOI：10.1021/ja983504u

  日期：1999.2.1

  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.