2'-deoxy-2'-[18F]fluoro-9-β-D-arabinofuranosyladenine | 173965-13-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-deoxy-2'-[18F]fluoro-9-β-D-arabinofuranosyladenine
• 英文别名: (18F)Fluorodeoxyadenosine；(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-(18F)fluoranyl-2-(hydroxymethyl)oxolan-3-ol
• CAS: 173965-13-4
• 化学式: C₁₀H₁₂FN₅O₃
• 分子量: 268.237
• InChiKey: ZGYYPTJWJBEXBC-JUVWDOIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  9-[(2R,3S,4R,5R)-3-(18F)fluoranyl-4-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]-N-[(4-methoxyphenyl)-diphenylmethyl]purin-6-amine 在 盐酸 作用下， 以 水 为溶剂， 生成 2'-deoxy-2'-[18F]fluoro-9-β-D-arabinofuranosyladenine
  参考文献：
  名称：

  Synthesis of deuterated 4,4?-diaminodiphenylsulfone (Dapsone) and related analogs

  摘要：

  描述了一种从苯胺-d5 合成4,4'-二氨基二苯基硫氧烷-d5（达普生）的通用方案。该方法可能具有普遍应用性，同时也描述了相关类似物的制备，即从苯胺-d5 合成4,4'-二甲基氨基二苯基硫氧烷和从酚-d5 合成4,4'-二甲氧基二苯基硫氧烷。版权© 2002 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.649

文献信息

• Synthesis of [18F]-labeled adenosine analogues as potential PET imaging agents
  作者：Mian M. Alauddin、John D. Fissekis、Peter S. Conti

  DOI：10.1002/jlcr.712

  日期：2003.8

  The syntheses of adenosine analogues, 2′-deoxy-2′-[18F]fluoro-9-β-D-arabinofuranosyladenine ([18F]-FAA) and 3′-deoxy-3′-[18F]fluoro-9-β-D-xylofuranosyladenine ([18F]-FXA) are reported. Adenosine (1) was converted to its methoxytrityl derivatives 2 and 3 as a mixture. After separation, these derivatives were converted to their respective triflates 4 and 5. Each triflate was reacted with tetrabutylammonium[18F]fluoride to produce 6b or 7b, which by acidic hydrolysis yielded compounds 8b and 9b. Crude preparations were purified by HPLC to obtain the desired pure products. The radiochemical yields were 10-18% decay corrected (d. c.) for 8b and 30-40% (d. c.) for 9b in 4 and 3 runs, respectively. Radiochemical purity was >99% and specific activity was >74 GBq/μmol at the end of synthesis (EOS). The synthesis time was 90-95 min from the end of bombardment (EOB). Copyright © 2003 John Wiley & Sons, Ltd.

  报道了腺苷类似物2′-脱氧-2′-[18F]氟-9-β-D-阿拉伯呋喃苷腺苷（[18F]-FAA）和3′-脱氧-3′-[18F]氟-9-β-D-木呋喃苷腺苷（[18F]-FXA）的合成。腺苷（1）被转化为其甲氧基三苯基衍生物2和3的混合物。分离后，这些衍生物被转化为各自的三氟化物4和5。每个三氟化物与四丁基氟铵[18F]反应生成6b或7b，随后通过酸性水解得到化合物8b和9b。粗制品通过高效液相色谱（HPLC）进行提纯，以获得所需的纯产品。8b的放射化学产率在4和3次反应中分别为10-18%（衰变校正，d.c.），9b的产率为30-40%（d.c.）。放射化学纯度超过99%，合成结束时（EOS）的比活性超过74 GBq/μmol。合成时间为从轰击结束（EOB）起90-95分钟。版权所有 © 2003 John Wiley & Sons, Ltd.