3-O-acetyl-5,6-dideoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-hexofuranose | 241148-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-5,6-dideoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-(2-fluoroethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 241148-75-4
• 化学式: C₁₁H₁₇FO₅
• 分子量: 248.251
• InChiKey: YCEJBGHQQIJEIT-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-5,6-dideoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-hexofuranose 在 Amberlite IR 120+> 作用下， 以 乙腈 为溶剂， 生成 5,6-dideoxy-6-fluoro-D-xylo-hexofuranose
  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
• 作为产物：
  描述：

  3-O-acetyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 在 吡啶 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3-O-acetyl-5,6-dideoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-hexofuranose
  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