6-O-(α-D-galactopyranosyl)-D-fructofuranose | 111188-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(α-D-galactopyranosyl)-D-fructofuranose
• 英文别名: melibiulose；syn planteobiose；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 111188-56-8
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: PVXPPJIGRGXGCY-XIOYNQKVSA-N

物化性质

• 沸点：
  784.8±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-(α-D-galactopyranosyl)-D-fructofuranose 在 4 A molecular sieve 、 Dowex 50 WX₄ H⁽¹⁺⁾ form 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以65%的产率得到5-[(α-D-galactopyranosyloxy)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
• 作为产物：
  描述：

  蜜二糖 在 sodium aluminate 作用下， 以 水 为溶剂， 反应 4.5h， 以82%的产率得到6-O-(α-D-galactopyranosyl)-D-fructofuranose
  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

• Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol
  作者：Da-Ming Gao、Takashi Kobayashi、Shuji Adachi

  DOI：10.1080/09168451.2015.1127135

  日期：2016.5.3

  Isomerization of disaccharides (maltose, isomaltose, cellobiose, lactose, melibiose, palatinose, sucrose, and trehalose) was investigated in subcritical aqueous ethanol. A marked increase in the isomerization of aldo-disaccharides to keto-disaccharides was noted and their hydrolytic reactions were suppressed with increasing ethanol concentration. Under any study condition, the maximum yield of keto-disaccharides produced from aldo-disaccharides linked by β-glycosidic bond was higher than that produced from aldo-disaccharides linked by α-glycosidic bond. Palatinose, a keto-disaccharide, mainly underwent decomposition rather than isomerization in subcritical water and subcritical aqueous ethanol. No isomerization was noted for the non-reducing disaccharides trehalose and sucrose. The rate constant of maltose to maltulose isomerization almost doubled by changing solvent from subcritical water to 80 wt% aqueous ethanol at 220 °C. Increased maltose monohydrate concentration in feed decreased the conversion of maltose and the maximum yield of maltulose, but increased the productivity of maltulose. The maximum productivity of maltulose was ca. 41 g/(h kg-solution).

  摘要：在亚临界水乙醇中研究了二糖（麦芽糖、异麦芽糖、赤霉糖、乳糖、甜菜碱、蔗糖和海藻糖）的异构化反应。注意到醛基二糖向酮基二糖的异构化明显增加，随着乙醇浓度的增加，它们的水解反应被抑制。在任何研究条件下，通过β-糖苷键连接的醛基二糖产生的酮基二糖的最大产量均高于通过α-糖苷键连接的醛基二糖产生的酮基二糖。在亚临界水和亚临界水乙醇中，酮基二糖甘露糖主要发生分解而非异构化。非还原性二糖海藻糖和蔗糖未观察到异构化。将溶剂从亚临界水改为80%乙醇水溶液后，麦芽糖向麦芽糖酮异构化的速率常数几乎翻倍，温度为220°C。在进料中增加麦芽糖单水合物浓度会降低麦芽糖的转化率和麦芽糖的最大产量，但会提高麦芽糖的生产率。麦芽糖的最大生产率约为41克/（小时·千克-溶液）。
• 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.