5-deoxy-5-fluoro-1,2-O-isopropylidene-β-L-idofuranose | 103357-79-5

• 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-β-L-idofuranose
• 英文别名: (3aR,5S,6R,6aR)-5-[(1S)-1-fluoro-2-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 103357-79-5
• 化学式: C₉H₁₅FO₅
• 分子量: 222.214
• InChiKey: LKISJBPRWHCLKT-TVNFTVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-fluoro-1,2-O-isopropylidene-β-L-idofuranose 在 sodium tetrahydroborate 、 3 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 5-deoxy-5-fluoro-1,2-O-isopropylidene-6-O-triphenylmethyl-β-L-talofuranose
  参考文献：
  名称：

  Synthetic applications of glucose isomerase: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

  摘要：

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00119-6
• 作为产物：
  描述：

  6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 3,5-cyclic sulfate 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-deoxy-5-fluoro-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Completely regioselective synthesis of 5- and 6- amino and fluoro-hexofuranoses via cyclic sulphates

  摘要：

  The nucleophilic opening of new and previously described 5,6- and 3,5-glucohexofuranose cyclic sulphates is a regioselective and efficient way to prepare 6- and 5-azido(amino)- and 6- and 5-fluoro-aldofuranose derivatives (D-gluco and L-ido configurations). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01529-9

文献信息

• Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol: Syntheses and glucosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-d-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-d-mannitol
  作者：Sören M. Andersen、Michael Ebner、Christian W. Ekhart、Günther Gradnig、Günter Legler、Inge Lundt、Arnold E. Stütz、Stephen G. Withers、Tanja Wrodnigg

  DOI：10.1016/s0008-6215(97)00099-2

  日期：1997.6

  1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannit and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconversion reactions as the key steps of the syntheses. Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3. (C) 1997 Elsevier Science Ltd.