9-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)-6-methoxypurine | 135473-16-4

• 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: 9-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)-6-methoxypurine
• 英文别名: tert-butyl-[[(2S,4S,5R)-4-fluoro-5-(6-methoxypurin-9-yl)oxolan-2-yl]methoxy]-dimethylsilane
• CAS: 135473-16-4
• 化学式: C₁₇H₂₇FN₄O₃Si
• 分子量: 382.51
• InChiKey: YPSVPQXRKGKOLH-MQIPJXDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)-6-methoxypurine 在 ammonium hydroxide 、 sodium hydroxide 作用下， 生成 9-[(2R,3S,5S)-3-氟-5-(羟基甲基)四氢呋喃-2-基]-3H-嘌呤-6-酮
  参考文献：
  名称：

  Deoxyfluoronucleoside process

  摘要：

  揭示了一种合成肌苷和腺嘌呤的2'-氟-2',3'-二去氧阿拉伯呋喃糖衍生物的大规模过程，涉及将氟糖衍生物和嘌呤试剂偶联以提供嘌呤核苷中间体，然后对其进行脱氧。6-氯或6-苯甲酰基嘌呤和1,3,5-三-O-苯甲酰-2-脱氧-2-氟阿拉伯呋喃糖被用作起始物质。

  公开号：

  EP0428109A3
• 作为产物：
  描述：

  dithiocarbonic acid O-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-5-(6-methoxy-purin-9-yl)-tetrahydro-furan-3-yl] ester S-methyl ester 以 二乙二醇二甲醚 为溶剂， 反应 4.0h， 以91%的产率得到9-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)-6-methoxypurine
  参考文献：
  名称：

  The “β-Fluorine Effect” in the Non-Metal Hydride Radical Deoxygenation of Fluorine-Containing Nucleoside Xanthates

  摘要：

  An alternative method to conduct a Barton-McCombie deoxygenation in nucleosides Is described. The utility of the procedure is limited to structures with an electronegative substituent, particularly fluorine, in the beta-position relative to the radical center. The process is radical in nature and triggered by peroxides. The abstraction of hydrogen from the solvent is favorably influenced by the presence of a beta-fluorine.

  DOI：

  10.1080/15257770008032993

文献信息

• Deoxyfluoronucleoside process
  申请人：Bristol-Myers Squibb Company

  公开号：EP0428109A3

  公开（公告）日：1991-09-11

  There is disclosed a process for synthesizing 2′-­fluoro-2′,3′-dideoxyarabinofuranose derivatives of inosine and adenine on a large scale which involves coupling of a fluorosugar derivative and a purine reactant to provide a purine nucleoside intermediate which is then deoxygenated. 6-Chloro or 6-benzamidopurine and 1,3,5-tri-O-benzoyl-2-­deoxy-2-fluoroarabinofuranose are used as starting materials.

  揭示了一种合成肌苷和腺嘌呤的2'-氟-2',3'-二去氧阿拉伯呋喃糖衍生物的大规模过程，涉及将氟糖衍生物和嘌呤试剂偶联以提供嘌呤核苷中间体，然后对其进行脱氧。6-氯或6-苯甲酰基嘌呤和1,3,5-三-O-苯甲酰-2-脱氧-2-氟阿拉伯呋喃糖被用作起始物质。
• The “β-Fluorine Effect” in the Non-Metal Hydride Radical Deoxygenation of Fluorine-Containing Nucleoside Xanthates
  作者：Maqbool A. Siddiqui、John S. Driscoll、Elie Abushanab、James A. Kelley、Joseph J. Barchi、Victor E. Marquez

  DOI：10.1080/15257770008032993

  日期：2000.1

  An alternative method to conduct a Barton-McCombie deoxygenation in nucleosides Is described. The utility of the procedure is limited to structures with an electronegative substituent, particularly fluorine, in the beta-position relative to the radical center. The process is radical in nature and triggered by peroxides. The abstraction of hydrogen from the solvent is favorably influenced by the presence of a beta-fluorine.