2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide | 1254190-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide
• CAS: 1254190-93-6
• 化学式: C₃₉H₄₅BrO₁₂
• 分子量: 785.683
• InChiKey: LBBONFMZVZYTPN-ANMRHESQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  134.28
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 在 甲醇 、 四丁基溴化铵 、 氢气 、 sodium methylate 、 palladium(II) hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 16.5h， 生成 kaempferol 3-O-neohesperidoside
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x
• 作为产物：
  描述：

  1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.5h， 生成 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x