6-azido-5,6-didesoxy-5-fluor-D-fructose | 134735-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-5,6-didesoxy-5-fluor-D-fructose
• 英文别名: 5,6-dideoxy-5-fluoro-6-azido-L-sorbose；(3S,4S,5R)-6-azido-5-fluoro-1,3,4-trihydroxyhexan-2-one
• CAS: 134735-67-4
• 化学式: C₆H₁₀FN₃O₄
• 分子量: 207.162
• InChiKey: QEYIQRLJXHBAIG-UYFOZJQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.1
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-5,6-didesoxy-5-fluor-D-fructose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-fluoro-1,2-dideoxynojirimycin
  参考文献：
  名称：

  Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors

  摘要：

  A combined fructose 1,6-diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6-deoxyazasugars were prepared by direct hydrogenolysis of the aldolase product without removal of the 6-phosphate group. Both (R)- and (S)-3-azido-2-acetamidopropanal used as substrates in the aldolase reactions were prepared from the corresponding lipase-resolved 2-hydroxy species followed by formation of an aziridine intermediate and opening of the aziridine with azide. Evaluation of these azasugars and their diastereomerically pure tertiary amine oxides as well as 5-thioglucose and its sulfoxide derivatives as glycosidase inhibitors was carried out. It was found that all synthetic azasugars and 5-thioglucose were strong inhibitors, but oxidation of the ring heteroatom weakened the inhibition. With the aid of molecular modeling and inhibition analysis, a structure-K(i) relation of inhibitors was established which provides useful information for the design of new glycosidase inhibitors.

  DOI：

  10.1021/ja00016a039
• 作为产物：
  描述：

  5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium azide 、 Amberlite IR-120 [H⁺] ion-exchange resin 、 immobilised glucose isomerase EC 5.3.1.5 (Sweetzyme T) 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 生成 6-azido-5,6-didesoxy-5-fluor-D-fructose
  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

表征谱图