N-alloc-tri-O-allyl-di-O-acetyl vancomycin aglycon allyl ester | 220971-87-9

• 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-tri-O-allyl-di-O-acetyl vancomycin aglycon allyl ester
• 英文别名: prop-2-enyl (1S,2R,18R,19R,22S,25R,28R,40S)-2,18-diacetyloxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-hydroxy-19-[[(2R)-4-methyl-2-[methyl(prop-2-enoxycarbonyl)amino]pentanoyl]amino]-20,23,26,42,44-pentaoxo-32,35,37-tris(prop-2-enoxy)-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),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylate
• CAS: 220971-87-9
• 化学式: C₇₃H₇₆Cl₂N₈O₂₁
• 分子量: 1472.35
• InChiKey: AERCLPDDZYYPII-DGBWLEODSA-N

物化性质

• 沸点：
  1500.4±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  104
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  393
• 氢给体数：
  8
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  phenyl 2-(4-azidobutyryl)-3,4,6-tri-O-acetyl-1-sulfinyl-β-D-glucopyranoside 、 N-alloc-tri-O-allyl-di-O-acetyl vancomycin aglycon allyl ester 在 三氟甲磺酸酐 、 2,6-dineopentylpyridine 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 生成 (2R)-N-[(1S,2R,18R,19R,22S,25R,28R,40S)-2,18-diacetyloxy-5,15-dichloro-48-[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(4-azidobutanoyloxy)oxan-2-yl]oxy-20,23,26,42,44-pentahydroxy-22-(2-hydroxy-2-iminoethyl)-32,35,37-tris(prop-2-enoxy)-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
  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：

  N-alloc-tri-O-allyl-O-PMB-di-O-acetyl vancomycin aglycon allyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以85%的产率得到N-alloc-tri-O-allyl-di-O-acetyl 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

• A Programmable One-Pot Oligosaccharide Synthesis for Diversifying the Sugar Domains of Natural Products: A Case Study of Vancomycin
  作者：Thomas K. Ritter、Kwok-Kong T. Mong、Haitian Liu、Takuji Nakatani、Chi-Huey Wong

  DOI：10.1002/anie.200351534

  日期：2003.10.6