dictyoglucosamine A | 426833-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dictyoglucosamine A
• 英文别名: (2S,3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-((propionyloxy)methyl)tetrahydro-2H-pyran-4-yl stearate；[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(propanoyloxymethyl)oxan-4-yl] octadecanoate
• CAS: 426833-52-5
• 化学式: C₂₉H₅₃NO₈
• 分子量: 543.742
• InChiKey: JMBNBSZNQHQINZ-VVTJRAGWSA-N

物化性质

• 沸点：
  674.3±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dictyoglucosamine A 在 硫酸 作用下， 以 甲醇 为溶剂， 以25%的产率得到[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] octadecanoate
  参考文献：
  名称：

  The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

  摘要：

  To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract or their fruit bodies, two novel acylated amino sugar were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-aceyl-D-glucosamine. Biological evaluation of 1 and 2 shocked the induce neuronal differentiation of rat pheochromocytoma (PC-12) cells. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00038-2
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-4-yl] octadecanoate 在 Wilkinson's catalyst 吡啶 、 三乙烯二胺 作用下， 以 乙醇 、 水 为溶剂， 生成 dictyoglucosamine A
  参考文献：
  名称：

  The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

  摘要：

  To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract or their fruit bodies, two novel acylated amino sugar were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-aceyl-D-glucosamine. Biological evaluation of 1 and 2 shocked the induce neuronal differentiation of rat pheochromocytoma (PC-12) cells. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00038-2