5-O-acetyl-1,2-O-isopropylidene-β-D-fructopyranose | 108529-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-acetyl-1,2-O-isopropylidene-β-D-fructopyranose
• 英文别名: [(5S,6S,7S,8R)-6,7-dihydroxy-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decan-8-yl] acetate
• CAS: 108529-25-5
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: ZHMLGHAKMKXLCD-REIXXSIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-1,2-O-isopropylidene-β-D-fructopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到1,2-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  3,4-Anhydro-1,2-O-isopropylidene-β-d-tagatopyranose and 4,5-anhydro-1,2-O-isopropylidene-β-d-fructopyranose

  摘要：

  3,4-Anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose (8) and 4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O- isopropylidene-4-O-toluene-p-sulfonyl-beta-D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl-1,2-O-isopropylidene-beta-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene-beta-D-tagatopyranose, respectively.

  DOI：

  10.1016/s0008-6215(99)00272-4
• 作为产物：
  描述：

  3,5-di-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-β-D-fructopyranose 在 sodium methylate 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 100.0h， 生成 5-O-acetyl-1,2-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  3,4-Anhydro-1,2-O-isopropylidene-β-d-tagatopyranose and 4,5-anhydro-1,2-O-isopropylidene-β-d-fructopyranose

  摘要：

  3,4-Anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose (8) and 4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O- isopropylidene-4-O-toluene-p-sulfonyl-beta-D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl-1,2-O-isopropylidene-beta-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene-beta-D-tagatopyranose, respectively.

  DOI：

  10.1016/s0008-6215(99)00272-4