3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose | 188540-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose
• CAS: 188540-59-2
• 化学式: C₁₂H₁₇FO₇S
• 分子量: 324.327
• InChiKey: HVOAYSLYWZZMCQ-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.13
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose 在 吡啶 、 N-氯代丁二酰亚胺 、 potassium methanolate 、 三氧化硫吡啶 、 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 2-deoxy-2-fluoro-glucotropaeolin
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

  摘要：

  S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-beta-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-beta-D-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00294-7
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 在 吡啶 、 Amberlite IRN 77 (H⁺ form) 、 硫化氢 、 sodium methylate 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

  摘要：

  S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-beta-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-beta-D-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00294-7

文献信息

• Direct radiolabelling of proteins at cysteine using [18F]-fluorosugars
  作者：Omar Boutureira、Gonçalo J. L. Bernardes、François D'Hooge、Benjamin G. Davis

  DOI：10.1039/c1cc13524d

  日期：——

  A strategy for the site-specific attachment of 2-deoxy-2-fluorosugars to cysteine and dehydroalanine tagged proteins is reported. When combined with thionation of fluorosugars, such as the widely available 18F probe 2-deoxy-2-[18F]fluoroglucose ([18F]FDG), this methodology allows fast and direct access to site-specific [18F]FDG-labelled proteins.

  报告了一种将 2-脱氧-2-氟糖特异性地连接到半胱氨酸和脱氢丙氨酸标记蛋白质上的策略。当与氟糖的硫离子化结合时，如广泛使用的 18F 探针 2-脱氧-2-[18F]氟葡萄糖（[18F]FDG），这种方法可以快速、直接地获得特定位点的[18F]FDG 标记蛋白质。