5-[(β-D-xylopyranosyloxy)methyl]-2-furancarboxaldehyde | 42400-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(β-D-xylopyranosyloxy)methyl]-2-furancarboxaldehyde
• 英文别名: 5-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]furan-2-carbaldehyde
• CAS: 42400-61-3
• 化学式: C₁₁H₁₄O₇
• 分子量: 258.228
• InChiKey: LZTYKXLWVKRTQQ-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[(β-D-xylopyranosyloxy)methyl]-2-furancarboxaldehyde 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以 水 为溶剂， 反应 36.0h， 以62%的产率得到
  参考文献：
  名称：

  HMF derivatives as platform molecules: aqueous Baylis–Hillman reaction of glucosyloxymethyl-furfural towards new biobased acrylates

  摘要：

  一种新型的生物基丙烯酸酯通过Baylis-Hillman反应，由异麦芽糖一步法可得的α-D-葡糖基甲氧甲基呋喃(α-GMF)与烷基丙烯酸酯合成。该反应在水相介质中进行，并扩展到其他α,β-不饱和底物。研究了使用二甲基异山梨酯作为共溶剂的应用。

  DOI：

  10.1039/c3ra43369b
• 作为产物：
  描述：

  primeverose 在 sodium aluminate 、 4 A molecular sieve 、 Dowex 50 WX₄ H⁽¹⁺⁾ form 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 7.5h， 生成 5-[(β-D-xylopyranosyloxy)methyl]-2-furancarboxaldehyde
  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.
• HMF derivatives as platform molecules: aqueous Baylis–Hillman reaction of glucosyloxymethyl-furfural towards new biobased acrylates
  作者：Jia-Neng Tan、Mohammed Ahmar、Yves Queneau

  DOI：10.1039/c3ra43369b

  日期：——

  A new type of biobased acrylates has been synthesized by a Baylis–Hillman reaction of alkylacrylates with α-D-glucosyloxymethyl-furfural (α-GMF), available in one step from isomaltulose. The reaction, performed in aqueous medium, was extended to other α,β-unsaturated substrates. The use of dimethylisosorbide as co-solvent was investigated.

  一种新型的生物基丙烯酸酯通过Baylis-Hillman反应，由异麦芽糖一步法可得的α-D-葡糖基甲氧甲基呋喃(α-GMF)与烷基丙烯酸酯合成。该反应在水相介质中进行，并扩展到其他α,β-不饱和底物。研究了使用二甲基异山梨酯作为共溶剂的应用。