(1S,2S,3R,4R,16S,17R,18R,21S,24S,25S,26R,27R,39S,40R,41R,44S)-2,3,17,18,25,26,40,41-octakis(phenylmethoxy)-6,15,20,22,29,38,43,45,47,49,50,52-dodecaoxanonacyclo[42.2.2.221,24.11,4.124,27.08,13.016,21.031,36.039,44]dopentaconta-8,10,12,31,33,35-hexaene | 1020076-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4R,16S,17R,18R,21S,24S,25S,26R,27R,39S,40R,41R,44S)-2,3,17,18,25,26,40,41-octakis(phenylmethoxy)-6,15,20,22,29,38,43,45,47,49,50,52-dodecaoxanonacyclo[42.2.2.221,24.11,4.124,27.08,13.016,21.031,36.039,44]dopentaconta-8,10,12,31,33,35-hexaene
• CAS: 1020076-15-6
• 化学式: C₉₆H₁₀₀O₂₀
• 分子量: 1573.84
• InChiKey: MBBYQMHTZNROAM-JBBGWLRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  116
• 可旋转键数：
  24
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  185
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,16S,17R,18R,21S,24S,25S,26R,27R,39S,40R,41R,44S)-2,3,17,18,25,26,40,41-octakis(phenylmethoxy)-6,15,20,22,29,38,43,45,47,49,50,52-dodecaoxanonacyclo[42.2.2.221,24.11,4.124,27.08,13.016,21.031,36.039,44]dopentaconta-8,10,12,31,33,35-hexaene 在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以99%的产率得到α-D-fructofuranose β-D-fructopyranose 1,2':2,1'-dianhydride
  参考文献：
  名称：

  Stereoselective synthesis of nonsymmetrical difructose dianhydrides from xylylene-tethered d-fructose precursors

  摘要：

  Nonsymmetrical furanose-pyranose difructose dianhydrides (DFAs), a class of cyclic disaccharides present in foodstuffs, have been prepared in high yield by connecting the reacting monosaccharide moieties through a xylylene bridge prior to triflic acid-promoted bis-spiroketalization. The reaction can then proceed either intra- or intermolecularly, both the regio- and the stereoselectivity being strongly dependent on the spacer length. Noteworthy, the longer m- and p-xylylene positional isomers led to the thermodynamic alpha-D-fructofuranose beta-D-fructopyranose 1,2':2,1'-dyanhydride 1, the major DFA in commercial caramel, in a stereoselective manner. The shorter o-xylylene tether afforded preferentially the elusive contra-thermodynamic beta-D-fructofuranose alpha-D-fructopyranose diastereomer 2, a trace constituent of caramel. The results have been rationalized in terms of stereoelectronic and conformational properties and offer new perspectives for the preparation of pure DFA standards for analytical and nutritional studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.054
• 作为产物：
  描述：

  在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到
  参考文献：
  名称：

  Stereoselective synthesis of nonsymmetrical difructose dianhydrides from xylylene-tethered d-fructose precursors

  摘要：

  Nonsymmetrical furanose-pyranose difructose dianhydrides (DFAs), a class of cyclic disaccharides present in foodstuffs, have been prepared in high yield by connecting the reacting monosaccharide moieties through a xylylene bridge prior to triflic acid-promoted bis-spiroketalization. The reaction can then proceed either intra- or intermolecularly, both the regio- and the stereoselectivity being strongly dependent on the spacer length. Noteworthy, the longer m- and p-xylylene positional isomers led to the thermodynamic alpha-D-fructofuranose beta-D-fructopyranose 1,2':2,1'-dyanhydride 1, the major DFA in commercial caramel, in a stereoselective manner. The shorter o-xylylene tether afforded preferentially the elusive contra-thermodynamic beta-D-fructofuranose alpha-D-fructopyranose diastereomer 2, a trace constituent of caramel. The results have been rationalized in terms of stereoelectronic and conformational properties and offer new perspectives for the preparation of pure DFA standards for analytical and nutritional studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.054

文献信息

• Stereoselective synthesis of nonsymmetrical difructose dianhydrides from xylylene-tethered d-fructose precursors
  作者：Farida Louis、M. Isabel García-Moreno、Patricia Balbuena、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1016/j.tet.2008.01.054

  日期：2008.3

  Nonsymmetrical furanose-pyranose difructose dianhydrides (DFAs), a class of cyclic disaccharides present in foodstuffs, have been prepared in high yield by connecting the reacting monosaccharide moieties through a xylylene bridge prior to triflic acid-promoted bis-spiroketalization. The reaction can then proceed either intra- or intermolecularly, both the regio- and the stereoselectivity being strongly dependent on the spacer length. Noteworthy, the longer m- and p-xylylene positional isomers led to the thermodynamic alpha-D-fructofuranose beta-D-fructopyranose 1,2':2,1'-dyanhydride 1, the major DFA in commercial caramel, in a stereoselective manner. The shorter o-xylylene tether afforded preferentially the elusive contra-thermodynamic beta-D-fructofuranose alpha-D-fructopyranose diastereomer 2, a trace constituent of caramel. The results have been rationalized in terms of stereoelectronic and conformational properties and offer new perspectives for the preparation of pure DFA standards for analytical and nutritional studies. (C) 2008 Elsevier Ltd. All rights reserved.