1,4,5-tri-O-benzoyl-2,3-O-isopropylidene-β-D-fructopyranose | 198215-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,5-tri-O-benzoyl-2,3-O-isopropylidene-β-D-fructopyranose
• CAS: 198215-65-5
• 化学式: C₃₀H₂₈O₉
• 分子量: 532.547
• InChiKey: CJRRZLCVIHANFM-ZRIOWSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,4,5-tri-O-benzoyl-2,3-O-isopropylidene-β-D-fructopyranose 在 三氟乙酸 作用下， 反应 0.5h， 以90%的产率得到1,4,5-tri-O-benzoyl-α,β-D-fructopyranose
  参考文献：
  名称：

  Synthesis of hydroxylated derivatives of topiramate, a novel antiepileptic drug based on d-fructose: Investigation of oxidative metabolites

  摘要：

  To corroborate the structures of two monohydroxylated metabolites of topiramate (1), we synthesized four monosaccharide derivatives from D-fructose: 4,5-O-[(1R*)- and 4,5-O-[(1S* )-1-hydroxymethylethylidene]-2,3-O-isopropylidene-beta-D-fructopyranose sulfamates (2a and 2b); 2,3-O-[(1R*)- and 2,3-O-[(1R*)-1-hydroxymethylethylidene]-4,5-O-isopropylidene-beta-D-fructopyranose sulfamates (3a and 3b). The route to 2a and 2b was brief and straightforward, while that to 3a and 3b was more involved. In the latter case, the D-fructose bis-acetal 10 was benzylated and converted to a monoacetal dibenzoate (14) (50% yield), which was then transacetalized to give a mixture of 4,5-dibenzoyl-2,3-O-[(1R*)- and 4,5-dibenzoyl-2,3-O-[(1S* )-1-benzyloxymethylethylidene]-beta-D-fructopyranose (16a and 16b) (22%). The individual diastereomers were separated and processed via ester saponification, acetonation, sulfamoylation, and hydrogenolysis into 3a (36%) and 3b (27%). Structure 2b was confirmed for one oxidative metabolite, but the other metabolite was found not to correspond with either 2a, 3a, or 3b. On the basis of CI-MS and H-1 NMR data, a (2-hydroxy-1,4-dioxano)pyran structure, 4, is proposed for this unidentified metabolite. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00214-0
• 作为产物：
  描述：

  果糖二丙酮 在 盐酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1,4,5-tri-O-benzoyl-2,3-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis of hydroxylated derivatives of topiramate, a novel antiepileptic drug based on d-fructose: Investigation of oxidative metabolites

  摘要：

  To corroborate the structures of two monohydroxylated metabolites of topiramate (1), we synthesized four monosaccharide derivatives from D-fructose: 4,5-O-[(1R*)- and 4,5-O-[(1S* )-1-hydroxymethylethylidene]-2,3-O-isopropylidene-beta-D-fructopyranose sulfamates (2a and 2b); 2,3-O-[(1R*)- and 2,3-O-[(1R*)-1-hydroxymethylethylidene]-4,5-O-isopropylidene-beta-D-fructopyranose sulfamates (3a and 3b). The route to 2a and 2b was brief and straightforward, while that to 3a and 3b was more involved. In the latter case, the D-fructose bis-acetal 10 was benzylated and converted to a monoacetal dibenzoate (14) (50% yield), which was then transacetalized to give a mixture of 4,5-dibenzoyl-2,3-O-[(1R*)- and 4,5-dibenzoyl-2,3-O-[(1S* )-1-benzyloxymethylethylidene]-beta-D-fructopyranose (16a and 16b) (22%). The individual diastereomers were separated and processed via ester saponification, acetonation, sulfamoylation, and hydrogenolysis into 3a (36%) and 3b (27%). Structure 2b was confirmed for one oxidative metabolite, but the other metabolite was found not to correspond with either 2a, 3a, or 3b. On the basis of CI-MS and H-1 NMR data, a (2-hydroxy-1,4-dioxano)pyran structure, 4, is proposed for this unidentified metabolite. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00214-0