Methanesulfonic acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester | 204633-61-4

• 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,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl] methanesulfonate
• CAS: 204633-61-4
• 化学式: C₃₉H₃₆FN₅O₈S
• 分子量: 753.808
• InChiKey: GBOBFYBOPMIYJM-MKAYBMDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  152.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-3-yl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 生成 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：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 三乙胺 作用下， 生成 Methanesulfonic acid (2R,3R,4R,5R)-5-(6-benzoylamino-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