1,5-anhydro-2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-fructopyranose | 871507-94-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,5-anhydro-2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-fructopyranose
• CAS: 871507-94-7
• 化学式: C₂₃H₃₂O₁₄
• 分子量: 532.499
• InChiKey: DXJRXYPIUROKCY-YEWOCYDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-fructopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以80%的产率得到1,5-anhydro-2,3-O-isopropylidene-4-O-β-D-glucopyranosyl-D-fructopyranose
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.03.005
• 作为产物：
  描述：

  1,5-anhydro-2,3-O-isopropylidene-β-D-fructopyranose 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到1,5-anhydro-2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-fructopyranose
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.03.005