1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructopyranose | 1168102-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructopyranose
• 英文别名: (4S,5S,6R)-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,3,4-triol
• CAS: 1168102-85-9
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: ZZIZYNWSCDRLDI-QMAVREKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  23
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  在 盐酸 、 水 、 乙醛 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以63%的产率得到1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructopyranose
  参考文献：
  名称：

  Convenient access to 4-O-glycosylated 1,5-anhydro-d-fructoses via disaccharide-derived 2-hydroxyglycal esters

  摘要：

  Efficient six-step protocols are described for the conversion of common disaccharides, such as maltose, cellobiose, or lactose, into the corresponding 4-O-glycosyl-1,5-anhydro-D-fructoses. Overall yields of 40-45% are favorably compared to the alternative eleven-step procedure from their monosaccharide components (similar to 15%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.005

文献信息

• Synthesis of 4-O-glycosylated 1,5-anhydro-d-fructose and of 1,5-anhydro-d-tagatose from a common intermediate 2,3-O-isopropylidene-d-fructose
  作者：Károly Agoston、Gyula Dékány、Inge Lundt

  DOI：10.1016/j.carres.2009.03.005

  日期：2009.5

  Four novel disaccharides of glycosylated 1,5-anhydro-D-ketoses have been prepared: 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-tagatose, and 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-beta-D-fructopyranose, was prepared from D-fructose and was converted into the D-tagatose derivative by oxidation followed by stereoselective reduction to the 4-epimer. The anhydroketoses thus prepared were glycosylated and deprotected to give the disaccharides. (C) 2009 Elsevier Ltd. All rights reserved.
• Convenient access to 4-O-glycosylated 1,5-anhydro-d-fructoses via disaccharide-derived 2-hydroxyglycal esters
  作者：Toshio Nakagawa、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2011.03.005

  日期：2011.4

  Efficient six-step protocols are described for the conversion of common disaccharides, such as maltose, cellobiose, or lactose, into the corresponding 4-O-glycosyl-1,5-anhydro-D-fructoses. Overall yields of 40-45% are favorably compared to the alternative eleven-step procedure from their monosaccharide components (similar to 15%). (C) 2011 Elsevier Ltd. All rights reserved.