2-O-(trifluoromethanesulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-(trifluoromethanesulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose
• 英文别名: [(2S,3R,4S,5R)-3,5-dibenzoyloxy-4-(trifluoromethylsulfonyloxy)oxolan-2-yl]methyl benzoate
• 化学式: C₂₇H₂₁F₃O₁₀S
• 分子量: 594.519
• InChiKey: HBSJRDYIAMPUCU-IMIIHFCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-O-(trifluoromethanesulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 、 胸腺嘧啶 在 kryptofix 222 、 potassium carbonate 、 氢氟酸 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 、 甲醇 、 potassium methanolate 作用下， 以 乙腈 、 1,4-二氧六环 为溶剂， 反应 1.08h， 以37.36%的产率得到2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil
  参考文献：
  名称：

  [EN] SYNTHESIS OF [18F] -LABELED THYMIDINE ANALOGUES
  [FR] SYNTHÈSE D'ANALOGUES DE THYMIDINE MARQUÉS [18F]

  摘要：

  Thymidine analogues, 5-substituted 2'-deoxy-2'-[18F]fluoro-arabinofuranosyluracil derivatives, are promising positron emission tomography (PET) tracers being evaluated for noninvasively imaging cancer cell proliferation and/or reporter gene expression. We report the radiosynthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]FMAU) and other 2'-deoxy-2'-[18F]fluoro-5-substituted-1-β-d-arabinofuranosyluracil analogues using 1,4-dioxane to replace the currently used 1,2-dichloroethane. Compared to 1,2-dichloroethane, 1,4-dioxane is analyzed as a better solvent in terms of radiosynthetic yield and toxicity concern. The use of a less toxic solvent allows for the translation of the improved approach to clinical production. The new radiolabeling method can be applied to an extensive range of uses for18F-labeling of other nucleoside analogues.

  公开号：

  WO2022109244A1

文献信息

• [EN] SYNTHESIS OF [18F] -LABELED THYMIDINE ANALOGUES<br/>[FR] SYNTHÈSE D'ANALOGUES DE THYMIDINE MARQUÉS [18F]
  申请人：[en]UNIVERSITY OF SOUTHERN CALIFORNIA

  公开号：WO2022109244A1

  公开（公告）日：2022-05-27

  Thymidine analogues, 5-substituted 2'-deoxy-2'-[18F]fluoro-arabinofuranosyluracil derivatives, are promising positron emission tomography (PET) tracers being evaluated for noninvasively imaging cancer cell proliferation and/or reporter gene expression. We report the radiosynthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]FMAU) and other 2'-deoxy-2'-[18F]fluoro-5-substituted-1-β-d-arabinofuranosyluracil analogues using 1,4-dioxane to replace the currently used 1,2-dichloroethane. Compared to 1,2-dichloroethane, 1,4-dioxane is analyzed as a better solvent in terms of radiosynthetic yield and toxicity concern. The use of a less toxic solvent allows for the translation of the improved approach to clinical production. The new radiolabeling method can be applied to an extensive range of uses for18F-labeling of other nucleoside analogues.