N-alloc-tri-O-allyl-penta-O-acetyl vancomycin pseudoaglycon allyl ester | 216669-02-2

• 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-penta-O-acetyl vancomycin pseudoaglycon allyl ester
• 英文别名: (2R)-N-[(1S,2R,18R,19R,22S,25R,28R,40S)-2,18-diacetyloxy-5,15-dichloro-48-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-hydroxyoxan-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
• CAS: 216669-02-2
• 化学式: C₈₅H₉₂Cl₂N₈O₂₉
• 分子量: 1760.61
• InChiKey: KJQHXAFGFFGRCV-NFTNPTRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  124
• 可旋转键数：
  36
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  490
• 氢给体数：
  8
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  N-alloc-tri-O-allyl-penta-O-acetyl vancomycin pseudoaglycon allyl ester 、 phenyl 3-(N-allyloxycarbonyloxy)-4-O-acetyl-1-sulfinyl-2,3,6-trideoxy-3-C-methyl-L-lyxohexopyranoside 在 三氟甲磺酸酐 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到N,N'-dialloc-tri-O-allyl-hexa-O-acetyl vancomycin 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：

  N,N'-dialloc-tri-O-allyl-hexa-O-acetyl vancomycin allyl ester 在 三氟化硼乙醚 、 苯硫酚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以71%的产率得到N-alloc-tri-O-allyl-penta-O-acetyl vancomycin pseudoaglycon allyl ester
  参考文献：
  名称：

  Reconstruction of Vancomycin by Chemical Glycosylation of the Pseudoaglycon

  摘要：

  DOI：

  10.1021/ja982414m

文献信息

• Glycosylation of glycopeptides: a comparison of chemoenzymatic and chemical methods
  作者：Catherine Leimkuhler、Zhong Chen、Ryan G. Kruger、Markus Oberthür、Wei Lu、Christopher T. Walsh、Daniel Kahne

  DOI：10.1016/j.tetasy.2004.12.006

  日期：2005.1

  hard to explore carbohydrate diversity in biologically active glycosylated natural products and their derivatives. In this paper we compare the efficiency of chemical and enzymatic methods for glycosylation of glycopeptides related to vancomycin and describe the parameters that should be considered in designing synthetic approaches to glycosylated natural product derivatives.

  糖基化复杂分子仍然是主要的合成挑战，这使得难以探索具有生物活性的糖基化天然产物及其衍生物中的碳水化合物多样性。在本文中，我们比较了与万古霉素有关的糖肽的糖基化的化学和酶促方法的效率，并描述了设计糖基化天然产物衍生物的合成方法时应考虑的参数。