2-deoxy-2-fluoro-α-D-ribofuranose 1,3,5-tribenzoate | 704916-12-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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-deoxy-2-fluoro-α-D-ribofuranose 1,3,5-tribenzoate
• 英文别名: [(2R,3R,4R,5R)-3,5-Bis(benzoyloxy)-4-fluorooxolan-2-yl]methyl benzoate；[(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-fluorooxolan-2-yl]methyl benzoate
• CAS: 704916-12-1
• 化学式: C₂₆H₂₁FO₇
• 分子量: 464.447
• InChiKey: JOAHVPNLVYCSAN-PIXQIBFHSA-N

物化性质

• 沸点：
  584.1±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为产物：
  描述：

  1,3,5-三苯甲酰基-D-呋喃核糖 在 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以55%的产率得到2-deoxy-2-fluoro-α-D-ribofuranose 1,3,5-tribenzoate
  参考文献：
  名称：

  EP1568703

  摘要：

  公开号：

文献信息

• Process for the preparation of 2'-halo-beta-L-arabinofuranosyl nucleosides
  申请人：——

  公开号：US20030060622A1

  公开（公告）日：2003-03-27

  The present invention is directed to the process for the preparation of 2′-deoxy-2′-halo-&bgr;-L-arabinofuranosyl nucleosides, and in particular, 2′-deoxy-2′-fluoro-&bgr;-L-arabinofuranosyl thymine (L-FMAU), from L-arabinose, which is commercially available and less expensive than L-ribose or L-xylose, in ten steps. All of the reagents and starting materials are inexpensive and no special equipment is required to carry out the reactions.

  本发明涉及制备2'-脱氧-2'-卤代-β-L-阿拉伯呋喃核苷的过程，特别是从商业可获得且价格较低的L-阿拉伯糖制备2'-脱氧-2'-氟-β-L-阿拉伯呋喃胸苷（L-FMAU），共经过十个步骤。所有试剂和起始原料都廉价，并且不需要特殊设备来进行反应。
• Nucleosides for imaging and treatment applications
  申请人：The Government of the United States of America, Secretary of Health and Human Services

  公开号：US20020022001A1

  公开（公告）日：2002-02-21

  Methods of diagnosing and/or of treating tumors by administering a nucleoside analogue which is activated by thymidylate synthase and/or thymidine kinase enzyme into a diagnostic or toxic metabolite, and uridine analogue compounds, and compositions of same having a pharmaceutically acceptable carrier. For diagnostic applications, compounds containing a label and methods of use of such compounds are described.

  通过向患者施用由胸腺嘧啶酸合成酶和/或胸腺嘧啶激酶酶激活的核苷类似物，使其转化为诊断或毒性代谢产物，以及尿嘧啶类似物化合物，以及具有药学可接受载体的组合物，来诊断和/或治疗肿瘤的方法。对于诊断应用，描述了含有标签的化合物以及使用这些化合物的方法。
• Method of fluorination
  申请人：Hara Shoji

  公开号：US20060014972A1

  公开（公告）日：2006-01-19

  A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200° C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely.

  一种氟化方法，包括通过热力学或微波辐射或波长在微波区域附近的电磁波与一种通式为(I)的氟化试剂反应，反应单糖，低聚糖，多糖，由这些糖与蛋白质和脂质结合形成的复合糖和具有多元醇，醛，酮和多元醇的酸以及这些化合物的衍生物和缩聚物。根据该方法，可以在150到200°C的温度范围内安全地进行选择性的氟化反应，而在传统方法中难以进行。上述方法包括使用微波或波长在微波区域附近的电磁波辐射，可应用于除糖类以外的基质。当HF和碱组成的复合物在微波辐射下反应时，难以在传统方法中进行的特定位置的氟化反应高度选择性，高效地在短时间内安全进行。
• Method of treating hepatitis delta virus infection
  申请人：——

  公开号：US20020160980A1

  公开（公告）日：2002-10-31

  A method for the treatment for hepatitis delta infection in a host, that includes administering an effective amount of a nucleoside or a nucleoside analog that suppresses the expression of the hepatitis B surface or preS1 antigen in the host 100-fold or more relative to pretreatment values in vivo; or to not more than 1 microgram per milliliter in vivo. In a preferred embodiment, the nucleoside is L-FMAU, or a pharmaceutically acceptable salt or prodrug thereof.

  一种治疗宿主体内丁型肝炎感染的方法，包括在体内给予有效量的核苷或核苷类似物，使其在体内相对于治疗前的值下降100倍或更多，抑制宿主体内丙型肝炎表面或preS1抗原的表达；或在体内不超过1微克/毫升。在优选实施例中，核苷为L-FMAU或其药学上可接受的盐或前药。
• Nucleoside process
  申请人：Bristol-Myers Company

  公开号：EP0145978A2

  公开（公告）日：1985-06-26

  Process for producing 1-halo-2-deoxy-2-fluoroarabi- nofuranoside derivatives bearing protective ester groups from 1,3,5-tri-O-acylribofuranose; the 1-halo compounds are intermediates in the synthesis of therapeutically active nucleosidic compounds.

  从 1,3,5-三-O-酰基呋喃核糖生产带有保护性酯基的 1-卤代-2-脱氧-2-氟呋喃核糖苷衍生物的工艺；这些 1-卤代化合物是合成具有治疗活性的核苷化合物的中间体。