(3S,4S,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[(4-methoxyphenyl)methoxy]oxolane-2,3-diol | 220793-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[(4-methoxyphenyl)methoxy]oxolane-2,3-diol
• 英文别名: 1-(5'-deoxy-5'-fluoro-α-D-arabinofuranosyl)-2-nitroimidazole；1-α-D-(5-deoxy-5-fluoroarabinofuranosyl)-2-nitroimidazole；fluoroazomycin arabinoside；FAZA；(2S,3S,4S,5S)-2-(fluoromethyl)-5-(2-nitroimidazol-1-yl)oxolane-3,4-diol
• CAS: 220793-03-3
• 化学式: C₈H₁₀FN₃O₅
• 分子量: 247.183
• InChiKey: LPZSRGRDVVGMMX-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 吡啶 、 potassium fluoride 、 ammonium cerium (IV) nitrate 、 六乙基二硅氮烷 、 二乙胺基三氟化硫 、 氨 、 四丁基碘化铵 、 sodium hydride 、 苯甲酸 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 14.17h， 生成 (3S,4S,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[(4-methoxyphenyl)methoxy]oxolane-2,3-diol
  参考文献：
  名称：

  Improved synthesis of the hypoxia probe 5-deutero-5-fluoro-5-deoxy-azomycin arabinoside (FAZA) as a model process for tritium radiolabeling

  摘要：

  Tritium-labelled fluoroazomycin arabinoside, [H-3]-FAZA, is a useful probe for the investigation of hypoxia, furthermore it is safer and easier to handle than the PET tracer [F-18]-FAZA when used in cell based assays. The only known synthesis of deuterium- and tritium-labelled FAZA was re-investigated and optimized. Then, a new and improved synthesis of [H-2]-FAZA was developed as a model process for tritium radiolabelling. This novel synthesis is expected to greatly facilitate access to [H-3]-FAZA. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.06.013

文献信息

• METHOD FOR PREPARING [18F]FALLYPRIDE WITH LOW BASE CONCENTRATION
  申请人：Kim Sang Eun

  公开号：US20120178920A1

  公开（公告）日：2012-07-12

  A method for preparing [ 18 F]fallypride is disclosed, which comprises a first step for trapping a fluorine-18 to a polymer ion exchange cartridge; a second step for extraction of fluorine-18 by inputting low base concentrations: 5.0˜25 μL of 40% TBAHCO 3 or K2.2.2./K 2 CO 3 (5˜25 mg/0.5˜3.0 mg) as a phase-transfer catalyst in a mixture of alcohol/water (1.0/0.2 (v/v)) or alcohol as a solvent into the polymer ion exchange cartridge trapped by the fluorine-18; a third step for preparing a [ 18 F]fallypride product by removing the solvent from the trapped fluorine-18, by inputting tosylate precursor in CH 3 CN as a solvent into a reactor and by reacting the same for 5˜35 minutes at 50˜120° C.; and a fourth step for preparing a pure [ 18 F]fallypride by purifying the prepared [ 18 F]fallypride product.

  本发明公开了一种制备[18F]fallypride的方法，包括以下步骤：第一步，将氟-18捕获到聚合物离子交换柱中；第二步，通过输入低浓度碱基（40％TBAHCO3或K2.2.2./K2 （5〜25毫克/0.5〜3.0毫克）作为相转移催化剂在酒精/水（1.0/0.2（v/v））或酒精混合溶剂中，从捕获氟-18的聚合物离子交换柱中提取氟-18；第三步，通过将tosylate前体在CH3CN中作为溶剂输入到反应器中，并在50〜120°C下反应5〜35分钟，从捕获氟-18的聚合物离子交换柱中去除溶剂，制备[18F]fallypride产物；第四步，通过纯化制备的[18F]fallypride产物，制备纯净的[18F]fallypride。
• Fluoroazomycin arabinoside (FAZA): synthesis,2H and3H-labelling and preliminary biological evaluation of a novel 2-nitroimidazole marker of tissue hypoxia
  作者：P. Kumar、D. Stypinski、H. Xia、A. J. B. McEwan、H-J. Machulla、L. I. Wiebe

  DOI：10.1002/(sici)1099-1344(199901)42:1<3::aid-jlcr160>3.0.co;2-h

  日期：1999.1
• COMPOSITIONS COMPRISING PKM2 MODULATORS AND METHODS OF TREATMENT USING THE SAME
  申请人：Sumitomo Dainippon Pharma Oncology, Inc.

  公开号：EP3941463A1

  公开（公告）日：2022-01-26
• POLYMER MONOLITHS FOR SOLVENT EXCHANGE IN CONTINUOUS FLOW MICROFLUIDIC DEVICE
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150152206A1

  公开（公告）日：2015-06-04

  The present disclosure relates to the novel multistep procedure for preparation of polymer monoliths for use in solvent exchange, such as methods to exchange and activate fluoride ions on a flow through microfluidic chip for subsequent chemical synthesis. Methods according to the present disclosure include the application of such microfluidic platforms for rapid F18 radiosynthesis on a flow through microfluidic chip with high efficiency, followed by a subsequent nucleophilic fluorination reaction. Various other methods of exchanging and activating fluoride ions on a flow through microfluidic chip are also disclosed. Methods incorporating features of the present invention can be applicable to any flow through microfluidic device in any field, such as radiosyntheses, chemical syntheses, concentration of ions for environmental analyses and sample preparation such as concentrating minute amounts of analyte to improve the downstream detection.
• US8624039B2
  申请人：——

  公开号：US8624039B2

  公开（公告）日：2014-01-07