phenyl 3-(N-allyloxycarbonyloxy)-4-O-acetyl-1-sulfinyl-2,3,6-trideoxy-3-C-methyl-L-lyxohexopyranoside | 216669-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 3-(N-allyloxycarbonyloxy)-4-O-acetyl-1-sulfinyl-2,3,6-trideoxy-3-C-methyl-L-lyxohexopyranoside
• 英文别名: [(2S,3S,4S)-6-(benzenesulfinyl)-2,4-dimethyl-4-(prop-2-enoxycarbonylamino)oxan-3-yl] acetate
• CAS: 216669-08-8
• 化学式: C₁₉H₂₅NO₆S
• 分子量: 395.477
• InChiKey: IPDXVDLFLUENGY-QJVJYHFGSA-N

物化性质

• 沸点：
  552.7±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3-(N-allyloxycarbonyloxy)-4-O-acetyl-1-sulfinyl-2,3,6-trideoxy-3-C-methyl-L-lyxohexopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 63.58h， 生成 2-iodoethyl 2-O-(3-allyloxycarbonylamino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Structural requirements for VanA activity of vancomycin analogues

  摘要：

  We have prepared several sets of glycopeptide analogues in order to probe the molecular basis for the activity of derivatives that overcome vanA resistance. The results described in this paper provide compelling evidence that good vanA activity is due to a mechanism of action that does not involve peptide binding. Hypothesizing that this mechanism of action involves an interaction of the disaccharide portion of vancomycin analogues with bacterial transglycosylases, we have prepared a compound in which the vancomycin aglycone is coupled to a known transglycosylase inhibitor that is structurally unrelated to the disaccharides that have been previously investigated. The activity of this compound is excellent. This work provides a clear prescription for the design of better glycopeptide analogues. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00743-3
• 作为产物：
  描述：

  Acetic acid (2S,3S,4S)-4-allyloxycarbonylamino-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到phenyl 3-(N-allyloxycarbonyloxy)-4-O-acetyl-1-sulfinyl-2,3,6-trideoxy-3-C-methyl-L-lyxohexopyranoside
  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

• Hybrid Glycopeptide Antibiotics
  作者：Binyuan Sun、Zhong Chen、Ulrike S. Eggert、Simon J. Shaw、John V. LaTour、Daniel Kahne

  DOI：10.1021/ja0166693

  日期：2001.12.19