Methanesulfonic acid (2R,3R,4S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester

• 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: Methanesulfonic acid (2R,3R,4S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester
• 英文别名: Mes(-3)[DMT(-5)]D-Araf2F(b)-adenin-9-yl；[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl] methanesulfonate
• 化学式: C₃₂H₃₂FN₅O₇S
• 分子量: 649.7
• InChiKey: BJOYOFSMTUYVFC-IWQUTFRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-(9-((2R,3S,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-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 Methanesulfonic acid (2R,3R,4S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester
  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

文献信息

• [EN] METHOD FOR SYNTHESIZING 9-(2,3-DIDEOXY-2-FLUORO- beta -D-THREO-PENTOFURANOSYL)ADENINE ( beta -FddA)<br/>[FR] PROCEDE DE SYNTHESE DE LA 9-(2,3-DIDEOXY -2-FLUORO- beta -D-THREO-PENTOFLURANOSYL)ADENINE ( beta -FddA)
  申请人：——

  公开号：WO1999029702A2

  公开（公告）日：1999-06-17

  [EN] A new method for the preparation of the anti-HIV antiviral compound 9-(2,3-dideoxy-2-fluoro- beta -D-threo-pentofuranosyl)adenine ( beta -FddA) is provided. The method relies upon the stereospecific hydrogenation of 9-[2,3-dideoxy-2-fluoro- beta -D-glycero-pent-2-enofuranosyl]adenine or various derivatives thereof. The methods are expected to be suitable for the preparation of other antiviral 9-(2,3-dideoxy-2-fluoro- beta -D-threo-pentofuranosyl)purines, such as beta -FddG and beta -FddI.
  [FR] L'invention porte sur un nouveau procédé de préparation d'un composé antiviral anti-VIH, la 9-(2,3-didéoxy-2-fluoro- beta -D-thréo-pentofluranosyl)adénine ( beta -FddA) se basant sur l'hydrogénation stéréospécifique de la 9-[2,3-didéoxy -2-fluoro- beta -D-glycéro-pentofluranosyl]adénine ou de certains de ses dérivés. Le procédé est également applicable à la préparation d'autres composés antiviraux, les 9-(2,3-didéoxy-2-fluoro- beta -D-thréo-pentofluranosyl)purines, tels que la beta -FddG et la beta -FddI.
• 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
  作者：Maqbool A. Siddiqui、John S. Driscoll、Victor E. Marquez

  DOI：10.1016/s0040-4039(98)00014-8

  日期：1998.3

  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.