| 474427-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 474427-12-8
• 化学式: C₁₈H₁₈O₉
• 分子量: 378.336
• InChiKey: LGELHMAWOCAUAX-LESCRADOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以80%的产率得到2,3-di-O-acetyl-1-O-phenyl-Δd⁴-α-D-glucopyranuronic acid
  参考文献：
  名称：

  Synthesis of α-Glucuronic Acid and Amide Derivatives in the Presence of a Participating 2-Acyl Protecting Group

  摘要：

  [GRAPHICS]Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.

  DOI：

  10.1021/ol026629j
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1-O-phenyl-α-D-glucopyranuronic acid sodium salt 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 72.0h， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of α-Glucuronic Acid and Amide Derivatives in the Presence of a Participating 2-Acyl Protecting Group

  摘要：

  [GRAPHICS]Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.

  DOI：

  10.1021/ol026629j