methyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate | 76100-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate
• 英文别名: 6-Desoxy-6-fluor-2,3-O-isopropyliden-L-gulosonsaeuremethylester；methyl (3aR,5R,6S,6aS)-5-(fluoromethyl)-6-hydroxy-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxole-3a-carboxylate
• CAS: 76100-48-6
• 化学式: C₁₀H₁₅FO₆
• 分子量: 250.224
• InChiKey: FGRQMOPRXGQQGH-HEZDBXPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate 在 Amberlite JR 120 (H+-form) 、 水 作用下， 反应 4.0h， 生成 6-Desoxy-6-fluor-L-ascorbinsaeure
  参考文献：
  名称：

  6-脱氧-6-卤素-L-Ascorbinsäure的合成和本征交换†

  摘要：

  L-抗坏血酸的6-脱氧-6-卤代衍生物的合成及性质

  DOI：

  10.1002/hlca.19800630642
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate 在 吡啶 、 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 methyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate
  参考文献：
  名称：

  6-脱氧-6-卤素-L-Ascorbinsäure的合成和本征交换†

  摘要：

  L-抗坏血酸的6-脱氧-6-卤代衍生物的合成及性质

  DOI：

  10.1002/hlca.19800630642

文献信息

• Synthese und Eigenschaften von 6-Desoxy-6-halogen-Derivaten der<scp>L</scp>-Ascorbinsäure
  作者：Joseph Kiss、Klaus Peter Berg、Adolf Dirscherl、Willi E. Oberhänsli、Wolf Arnold

  DOI：10.1002/hlca.19800630642

  日期：1980.9.17

  Synthesis and Properties of 6-Deoxy-6-halogeno-Derivatives of L-Ascorbic Acid

  L-抗坏血酸的6-脱氧-6-卤代衍生物的合成及性质
• 6-Deoxy-6-fluoro-l-ascorbic acid: crystal structure and oxidative degradation
  作者：Janusz Madaj、Yoko Nishikawa、V.Prakash Reddy、Peter Rinaldi、Tadao Kurata、Vincent M. Monnier

  DOI：10.1016/s0008-6215(00)00183-x

  日期：2000.11

  Ascorbic acid and its oxidation products have been implicated in non-enzymatic modification of proteins in aging and diseases of oxidative stress. We have studied the feasibility of using 6-deoxy-6-fluoroascorbic acid (6) for identification of ascorbic acid degradation products by F-19 NMR spectroscopy. Crystals of compound 6 from nitromethane belonged to the space group P2(1) with a = 5.547(2), b = 6.769(3), c = 9.302(2) Angstrom, beta = 91.80(3)degrees and Z = 2. Atomic coordinates, bond lengths and angles, hydrogen coordinates, anisotropic and isotropic displacement parameters were similar if not identical with those of native ascorbic acid. Similarly, UV properties and oxidation kinetics by CuCl2 at different pH values were essentially identical with ascorbic acid. Using 750 MHz F-19 NMR spectroscopy, five to six new fluorinated products were detected after overnight oxidation of 6 with Cu2+, suggesting that 6 may be a powerful and sensitive tool for assessment of its catabolism in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.