5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose | 103357-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose
• CAS: 103357-82-0
• 化学式: C₉H₁₅FO₅
• 分子量: 222.214
• InChiKey: LKISJBPRWHCLKT-OZRXBMAMSA-N

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose 在 镍 吡啶 、 三氟化硼乙醚 、 氢气 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-acetyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of 5,6-dimodified open-chain d-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase

  摘要：

  5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodifed open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-difluoro derivatives, were synthesised employing glucose isomerase catalysed isomerisation of the corresponding D-xylo- and D-glucofuranoses as a key step. New compounds as well as some previously reported analogues such as 5-azido-5,6-dideoxy-6-fluoro-D- fructose were shown to be excellent substrates of polyol dehydrogenase from Burkholderia cepacia DSM 50181 with K-m values two orders of magnitude smaller than the corresponding natural substrates. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00526-1
• 作为产物：
  描述：

  (3aR,3bR,6S,6aS,7aR)-6-Fluoro-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives

  摘要：

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00255-3