2,6-dideoxy-2,6-difluoro-β-D-glucopyranosyl fluoride | 350600-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dideoxy-2,6-difluoro-β-D-glucopyranosyl fluoride
• 英文别名: (2S,3S,4S,5R,6S)-5,6-difluoro-2-(fluoromethyl)oxane-3,4-diol
• CAS: 350600-83-8
• 化学式: C₆H₉F₃O₃
• 分子量: 186.131
• InChiKey: BMXIFBPTUCGDMM-QZABAPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-5,6-Difluoro-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 在 吡啶 、 二乙胺基三氟化硫 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 2,6-dideoxy-2,6-difluoro-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Adam, Michael J.; Wong, Alexander W.; Withers, Stephen G., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S448 - S450

  摘要：

  DOI：

文献信息

• Synthesis of 2,6-dideoxy-2-fluoro-6-[18F]-fluoro-?-D-glucopyranosyl fluoride (2,6FGF) as a potential imaging probe for glucocerebrosidase
  作者：Alexander W. Wong、Michael J. Adam、Stephen G. Withers

  DOI：10.1002/jlcr.466

  日期：2001.4

  We have previously synthesized 2-deoxy-2-[18F]-fluoro-β-mannosyl [18F]-fluoride and shown that it behaves as a mechanism-based inhibitor of Agrobacterium sp. β-glucosidase. In-vivo experiments indicate that this compound undergoes partial hydrolysis to produce 2-deoxy-2-fluoro-mannose, which can become phosphorylated and trapped within the cell. We now report the synthesis of another 2-fluoro glycoside which is 18F-labelled at the 6 position so that the label cannot be lost during such glycoside hydrolysis and which, further, cannot be phosphorylated. The mechanism-based glycosidase inhibitor 2,6-dideoxy-2-fluoro-6-[18F]-fluoro-β-D-glucopyranosyl fluoride (2,6FGF) was synthesized in 69% overall chemical yield and in 9% radiochemical yield (decay corrected) as a potential imaging probe for glycosidase. Copyright © 2001 John Wiley & Sons, Ltd.

  我们之前合成了2-deoxy-2-[18F]-fluoro-β-mannosyl [18F]-氟化物，并证明其作为根肿瘤农杆菌β-葡萄糖苷酶的机制抑制剂。在体内实验中表明该化合物会部分水解，生成2-deoxy-2-fluoro-mannose，该物质可以被磷酸化并被困在细胞内。我们现在报告合成了另一种在6位标记有18F的2-fluoro糖苷，这样在糖苷水解过程中标签不会丢失，并且该化合物无法被磷酸化。机制基础的糖苷酶抑制剂2,6-脱氧-2-氟-6-[18F]-氟化β-D-葡萄糖吡喃糖苷氟化物（2,6FGF）以69%的总体化学产率和9%的放射化学产率（已校正衰变）合成，作为糖苷酶的潜在成像探针。版权 © 2001 John Wiley & Sons, Ltd.