2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-α-D-glucuronic acid allyl ester | 1122631-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-α-D-glucuronic acid allyl ester
• CAS: 1122631-48-4
• 化学式: C₃₀H₂₅BrO₉
• 分子量: 609.427
• InChiKey: WUNMJXBOHJNWPP-BONDPLATSA-N

物化性质

• 沸点：
  678.5±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-α-D-glucuronic acid allyl ester 在 silver carbonate 、 水 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以77%的产率得到
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h
• 作为产物：
  描述：

  (3R,4S,5S,6S)-6-((allyloxy)carbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-α-D-glucuronic acid allyl ester
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h