(R)-4-((S)-2-{(R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methoxy-3-octadecyloxy-propoxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester | 162678-86-6

• 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: (R)-4-((S)-2-{(R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methoxy-3-octadecyloxy-propoxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester
• CAS: 162678-86-6
• 化学式: C₄₈H₈₂N₄O₁₃
• 分子量: 923.198
• InChiKey: QAMBUNRTWZCHPV-LLUGWUAFSA-N

物化性质

• 沸点：
  1062.1±65.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  65.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  243.3
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((S)-2-{(R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methoxy-3-octadecyloxy-propoxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到(R)-4-((S)-2-{(R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methoxy-3-octadecyloxy-propoxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid
  参考文献：
  名称：

  Potential adjuvants for synthetic vaccines. I. Modulators of macrophage activation

  摘要：

  The synthesis and biological activities of several glycopeptidolipids derived from muramyl dipeptide (MDP) are described. In combination with gamma interferon (INF gamma) MDP derivatives 3c and 3d carrying glycyrrhetinic acid as rigid beta-aglycone synergise the action of the lymphokine in the release of H2O2 by activated human macrophages, while MDP derivatives 3a and 6a carrying the more flexible diphytanyl glycerol beta-aglycone inhibit it.

  DOI：

  10.1016/0009-3084(94)02400-y
• 作为产物：
  描述：

  L-alanyl-D-isoglutamine benzyl ester 在 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 (R)-4-((S)-2-{(R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methoxy-3-octadecyloxy-propoxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester
  参考文献：
  名称：

  Potential adjuvants for synthetic vaccines. I. Modulators of macrophage activation

  摘要：

  The synthesis and biological activities of several glycopeptidolipids derived from muramyl dipeptide (MDP) are described. In combination with gamma interferon (INF gamma) MDP derivatives 3c and 3d carrying glycyrrhetinic acid as rigid beta-aglycone synergise the action of the lymphokine in the release of H2O2 by activated human macrophages, while MDP derivatives 3a and 6a carrying the more flexible diphytanyl glycerol beta-aglycone inhibit it.

  DOI：

  10.1016/0009-3084(94)02400-y