9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-2,5-dihydro-furan-2-yl}-9H-purin-6-ylamine | 204633-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-2,5-dihydro-furan-2-yl}-9H-purin-6-ylamine
• 英文别名: 9-[(2R,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-fluoro-2,5-dihydrofuran-2-yl]purin-6-amine
• CAS: 204633-62-5
• 化学式: C₃₁H₂₈FN₅O₄
• 分子量: 553.593
• InChiKey: QYAZKOHYLDOAIZ-SETSBSEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-2,5-dihydro-furan-2-yl}-9H-purin-6-ylamine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以56%的产率得到2'-beta-氟-2',3'-二脱氧腺苷
  参考文献：
  名称：

  A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (β-FddA). Introduction of a 2′-β-fluoro substituent via inversion of a readily obtainable 2′-α-fluoro isomer

  摘要：

  A convenient route to the anti-HIV active compound, 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (1, beta-FddA) started with the facile introduction of fluorine at C2' from the alpha-side of protected 9-(beta-D-arabinofuranosyl)adenine (ara-A). Inversion of the stereochemistry at C2' was accomplished via a stable vinyl intermediate (6), which underwent stereoselective reduction of the double bond to give the desired 2'-F-threo isomer with the opposite beta-fluoro stereochemistry. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(98)00014-8
• 作为产物：
  描述：

  N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 在 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 9-{(2R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-2,5-dihydro-furan-2-yl}-9H-purin-6-ylamine
  参考文献：
  名称：

  A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (β-FddA). Introduction of a 2′-β-fluoro substituent via inversion of a readily obtainable 2′-α-fluoro isomer

  摘要：

  A convenient route to the anti-HIV active compound, 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (1, beta-FddA) started with the facile introduction of fluorine at C2' from the alpha-side of protected 9-(beta-D-arabinofuranosyl)adenine (ara-A). Inversion of the stereochemistry at C2' was accomplished via a stable vinyl intermediate (6), which underwent stereoselective reduction of the double bond to give the desired 2'-F-threo isomer with the opposite beta-fluoro stereochemistry. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(98)00014-8