5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-xylofuranose | 34147-20-1

• 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-xylofuranose
• 英文别名: 5-fluoro-O¹,O²-isopropylidene-α-D-5-deoxy-xylofuranose；(3aR,5S,6R,6aR)-5-(fluoromethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 34147-20-1
• 化学式: C₈H₁₃FO₄
• 分子量: 192.187
• InChiKey: MXKKVLFGAICJOI-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-xylofuranose 在 硫酸 作用下， 生成 5-Desoxy-5-fluoro-D-xylose-2,5-dichlorphenyl-hydrazon
  参考文献：
  名称：

  Fluorocarbohydrates—XXI

  摘要：

  DOI：

  10.1016/s0040-4020(01)98133-5
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-xylofuranose
  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

文献信息

• Synthesis of 5,6-dimodified open-chain d-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase
  作者：Philipp Hadwiger、Peter Mayr、Bernd Nidetzky、Arnold E Stütz、Andreas Tauss

  DOI：10.1016/s0957-4166(99)00526-1

  日期：2000.2

  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.
• WO2024073732A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives
  作者：Philipp Hadwiger、Peter Mayr、Andreas Tauss、Arnold E Stütz、Bernd Nidetzky

  DOI：10.1016/s0960-894x(99)00255-3

  日期：1999.6

  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.
• Fluorocarbohydrates—XXI
  作者：P.W. Kent、R.C. Young

  DOI：10.1016/s0040-4020(01)98133-5

  日期：1971.1