5-[(α-D-glucopyranuronosyloxy)methyl]-2-furoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(α-D-glucopyranuronosyloxy)methyl]-2-furoic acid
• 英文别名: (2S,3S,4S,5R,6S)-6-[(5-carboxyfuran-2-yl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₂H₁₄O₁₀
• 分子量: 318.237
• InChiKey: PCMJSMQENDKZQT-YIQYQHPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  167
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-(α-D-glucosyloxymethyl)furfural 在 platinum(IV) oxide 氧气 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 3.0h， 以84%的产率得到5-[(α-D-glucopyranuronosyloxy)methyl]-2-furoic acid
  参考文献：
  名称：

  Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals

  摘要：

  A practical protocol for the elaboration of O-glycosyl-HMF's from glycosyl-(1 -> 6)-glucoses is reported, the two steps involving aluminate-promoted isomerization to the respective 6-O-glycosyl-fructoses and subsequent selective dehydration of the fructose portion. Accordingly, melibiose, gentiobiose, and primeverose are converted into the corresponding 2-uloses and, then, into alpha-GalMF 11, beta-GMF 12, and beta-XylMF 13. Pt/C-catalyzed oxidation with oxygen in NaOH at 25 degrees C efficiently generated the respective furoic acids from alpha-GalMF and alpha-GMF, whilst Pt/O-2 in water at 50 degrees C also oxidizes the primary OH to give the dicarboxylic acids 15 and 17-key building blocks for the generation of novel types of polyesters and polyamides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.010

文献信息

• Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals
  作者：Dierk Martin、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2005.12.010

  日期：2006.3

  A practical protocol for the elaboration of O-glycosyl-HMF's from glycosyl-(1 -> 6)-glucoses is reported, the two steps involving aluminate-promoted isomerization to the respective 6-O-glycosyl-fructoses and subsequent selective dehydration of the fructose portion. Accordingly, melibiose, gentiobiose, and primeverose are converted into the corresponding 2-uloses and, then, into alpha-GalMF 11, beta-GMF 12, and beta-XylMF 13. Pt/C-catalyzed oxidation with oxygen in NaOH at 25 degrees C efficiently generated the respective furoic acids from alpha-GalMF and alpha-GMF, whilst Pt/O-2 in water at 50 degrees C also oxidizes the primary OH to give the dicarboxylic acids 15 and 17-key building blocks for the generation of novel types of polyesters and polyamides. (c) 2006 Elsevier Ltd. All rights reserved.