2-deoxy-2-fluoro-β-D-mannopyranose | 55449-80-4

• 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-mannopyranose
• 英文别名: 2-deoxy-2-fluoro-β-D-manopyranose；2-deoxy-2-fluoro-D-mannopyranose；2-fluoro-β-D-2-deoxy-mannopyranose；2-Deoxy-2-fluoro-beta-D-mannose；(2R,3S,4S,5S,6R)-3-fluoro-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 55449-80-4
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: ZCXUVYAZINUVJD-AIECOIEWSA-N

物化性质

• 沸点：
  413.6±45.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 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：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 Selectfluor 作用下， 以 硝基甲烷 、 重水 为溶剂， 反应 15.5h， 生成 2-deoxy-2-fluoro-β-D-mannopyranose
  参考文献：
  名称：

  D-葡萄糖及其衍生物与1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐的反应研究

  摘要：

  摘要利用19F NMR光谱研究了D-葡萄糖及其衍生物与亲电NF-氟化试剂F-TEDA四氟硼酸酯和三氟甲磺酸酯的反应。在所有情况下，均形成2-脱氧-2-氟-D-葡萄糖-和-D-甘露吡喃糖衍生物的混合物，其比例取决于O-保护基团的性质。关于直接通过双键添加试剂产生的产物，D-葡萄糖构型的化合物（13-20）通常显示出比其D-甘露聚糖对应物（21-28）更高的水解速率。仅当形成单个端基异构体（例如2,4-二硝基苯基糖苷29e / 37e和二糖氟化物35d / 43d）或过氧乙酸酯（例如29f / 37f）时，才能实现产品分离。

  DOI：

  10.1080/07328309908543997

文献信息

• Synthesis of 2-deoxy-2-fluorohexoses by fluorination of glycals in aqueous media
  作者：Mirko Diksic、Dean Jolly

  DOI：10.1016/s0008-6215(00)90191-5

  日期：1986.9

  and organic solvent-water with molecular fluorine and, for 18 F-labelled compounds, with [ 18 F]fluorine. Chemical yields of 40 and 10% were obtained for 2-deoxy-2-fluoro- d -glucose and 2-deoxy-2-fluoro- d -mannose, respectively, and 35 and 5% for 2-deoxy-2-fluoro- d -galactose ( 12 ) and 2-deoxy-2-fluoro- d -talose ( 13 ), respectively. In the fluorination of 3 , the chemical yields of 12 and 13 were

  摘要1,5-Anhydro-2-deoxy- d-arabino-（d -glucal），1,5-anhydro-2-deoxy- d-lyxo-（d -galactal）和3,4,6-tri-在水中和有机溶剂中对O-乙酰基1,5,5-脱水-2-脱氧-d-lyxo-己-1-烯醇（3,4,6-tri-O-乙酰基-d-半乳糖）（3）进行氟化-具有分子氟的水，以及对于18 F标记的化合物，具有[18 F]氟。2-脱氧-2-氟-d-葡萄糖和2-脱氧-2-氟-d-甘露糖的化学收率分别为40％和10％，2-脱氧-2-氟-d-甘露糖的化学收率分别为35％和5％。 d-半乳糖（12）和2-脱氧-2-氟-d-塔洛糖（13）。在氟化3中，化学产率12和13分别为38和6％。描述了2-脱氧-2-氟-d-己糖的1c分离。
• Metabolic pathway of 2-deoxy-2-fluoro-D-glucose and 2-deoxy-2-fluoro-D-mannose in mice bearing sarcoma 180 studied by fluorin-19 nuclear magnetic resonance.
  作者：MASAHARU KOJIMA、SATORU KURIBAYASHI、YOKO KANAZAWA、TERUSHI HARADAHIRA、YOSHIHIKO MAEHARA、HIDEYA ENDO

  DOI：10.1248/cpb.36.1194

  日期：——

  The metabolic products of 2-deoxy-2-fluoro-D-glucose (FDG) and 2-deoxy-2-fluoro-D-mannose (FDM) in sarcoma 180 cells transplanted in mice were investigated by fluorin-19 nuclear magnetic resonance (19F-NMR) spectroscopy. It became apparent that the administered FDG was converted to FDM (and/or FDM-6-phosphate) in tumor cells, and also the administered FDM was converted to FDG (and/or FDG-6-phosphate). At 9h after administration of FDM, the ratio of FDG (and/or FDG-6-phosphate) and FDM (and/or FDM-6-phosphate) reached equilibrium. On the other hand, it took more than 48h in the case of FDG administration. The equilibrium amount of FDM (and/or FDM-6-phosphate) was approximately four times as much as that of FDG (and/or FDG-6-phosphate) in both cases.

  通过氟-19核磁共振（19F-NMR）光谱研究了在小鼠体内移植的肉瘤180细胞中2-脱氧-2-氟-D-葡萄糖（FDG）和2-脱氧-2-氟-D-甘露糖（FDM）的代谢产物。结果表明，所施用的FDG在肿瘤细胞中转化为FDM（和/或FDM-6-磷酸），施用的FDM也转化为FDG（和/或FDG-6-磷酸）。施用FDM后9小时，FDG（和/或FDG-6-磷酸）与FDM（和/或FDM-6-磷酸）的比例达到平衡。另一方面，施用FDG后需要超过48小时。在这两种情况下，FDM（和/或FDM-6-磷酸）的平衡量大约是FDG（和/或FDG-6-磷酸）的四倍。
• Polymerizable monomers and process of preparation thereof
  申请人：——

  公开号：US20040192905A1

  公开（公告）日：2004-09-30

  The present invention relates to polymerizable monomers for applications in medicine and biotechnology and synthesis thereof. The polymerizable ligands containing NAcetyl Glucosamine bind more strongly to lysozyme than NAG itself. The binding is further enhanced when a spacer arm, for example 6-Amino Caproic Acid (6-ACA) is introduced in the structure. The conjugated ligands could be used for prevention and treatment of bacterial and viral infections Moreover these ligands can be coupled to stimuli sensitive polymers and used for the recovery of biomolecules The methodology can be extended to other ligands such as sialic acid and the corresponding polymers used for preventil1g influenza and lor rotavirus infections

  本发明涉及用于医学和生物技术应用的可聚合单体及其合成方法。含有N-乙酰葡萄糖胺的可聚合配体比NAG本身更强烈地结合于溶菌酶。当引入一个间隔臂，例如6-氨基己酸（6-ACA）时，结合进一步增强。这些共轭配体可用于预防和治疗细菌和病毒感染。此外，这些配体可以与刺激敏感聚合物耦合，并用于恢复生物分子。该方法可以扩展到其他配体，例如唾液酸，相应的聚合物可用于预防流感和轮状病毒感染。
• [EN] POLYMERIZABLE MONOMERS AND PROCESS OF PREPARATION THEREOF<br/>[FR] MONOMERES POLYMERISABLES ET LEUR PROCEDE DE PREPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004087725A1

  公开（公告）日：2004-10-14

  The present invention relates to polymerizable monomers for applications in medicine and biotechnology and synthesis thereof. The polymerizable ligands containing NAcetyl Glucosamine bind more strongly to lysozyme than NAG itself. The binding is further enhanced when a spacer arm, for example 6- Amino Caproic Acid (6-ACA) is introduced in the structure. The conjugated ligands could be used for prevention and treatment of bacterial and viral infections. Moreover these ligands can be coupled to stimuli sensitive polymers and used for the recovery of biomolecules. The methodology can be extended to other ligands such as sialic acid and the corresponding polymers used for preventilIg influenza and for rotavirus infections.

  本发明涉及用于医学和生物技术应用的可聚合单体及其合成。含有N-乙酰葡萄糖胺的聚合物配体比NAG本身更强烈地结合溶菌酶。当引入一个空间臂，例如6-氨基己酸（6-ACA）时，结合进一步增强。这些共轭配体可用于预防和治疗细菌和病毒感染。此外，这些配体可以与刺激敏感性聚合物结合，并用于生物分子的恢复。该方法可以扩展到其他配体，例如唾液酸和相应的聚合物可用于预防流感和轮状病毒感染。
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。