2-deoxy-2-fluoro-β-D-glucopyranosyl fluoride | 103960-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-fluoro-β-D-glucopyranosyl fluoride
• 英文别名: 2-Deoxy-2-fluoro-alpha-D-mannosyl fluoride；(2R,3S,4S,5R,6S)-5,6-difluoro-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 103960-04-9
• 化学式: C₆H₁₀F₂O₄
• 分子量: 184.14
• InChiKey: YZRDPODBASCWCK-QZABAPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  69.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-fluoro-β-D-glucopyranosyl fluoride 在 甲醇 、 三氟化硼乙醚 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3,4-di-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of 2,6-dideoxy-2-fluoro-6-[18F]-fluoro-?-D-glucopyranosyl fluoride (2,6FGF) as a potential imaging probe for glucocerebrosidase

  摘要：

  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.

  DOI：

  10.1002/jlcr.466

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.
• AMYLASE INHIBITOR COMPOUNDS, METHODS OF THEIR USE AND COMPOSITIONS THEREOF
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：US20200079810A1

  公开（公告）日：2020-03-12

  There are provided compounds of Formula I: various compositions thereof and methods for their use in the inhibition of α-amylase.

  提供了式I的化合物：它们的各种组合以及在抑制α-淀粉酶方面使用它们的方法。
• WITHERS, STEPHEN G.;WARREN, R. ANTONY J.;STREET, IAN P.;RUPITZ, KAREN;KEM+, J. AMER. CHEM. SOC. , 112,(1990) N5, C. 5887-5889
  作者：WITHERS, STEPHEN G.、WARREN, R. ANTONY J.、STREET, IAN P.、RUPITZ, KAREN、KEM+

  DOI：——

  日期：——
• Unequivocal demonstration of the involvement of a glutamate residue as a nucleophile in the mechanism of a retaining glycosidase
  作者：Stephen G. Withers、R. Antony J. Warren、Ian P. Street、Karen Rupitz、Julie B. Kempton、Ruedi Aebersold

  DOI：10.1021/ja00171a043

  日期：1990.7
• ASPEGILLUS NIGER BETA-GLUCOSIDASE GENE, PROTEIN AND USES THEREOF
  申请人：Yissum Research and Development Company of the Hebrew University of Jerusalem

  公开号：EP1230343A2

  公开（公告）日：2002-08-14