(R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-1-(2,6-diethylpyridin-4-yl)-5-oxopent-1-yn-3-yl acetate | 1508318-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-1-(2,6-diethylpyridin-4-yl)-5-oxopent-1-yn-3-yl acetate
• CAS: 1508318-98-6
• 化学式: C₃₁H₃₆N₂O₅
• 分子量: 516.637
• InChiKey: WIBYIYAZEGDWLL-QCENPCRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  85.8
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-1-(2,6-diethylpyridin-4-yl)-5-oxopent-1-yn-3-yl acetate 、 对甲苯磺酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 异丙醇 、 甲苯 、 四氢呋喃 为溶剂， -10.0~45.0 ℃ 、446.08 kPa 条件下， 以11.95 kg的产率得到(R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-5-(2,6-diethylpyridin-4-yl)-1-oxopentan-3-yl acetate tosylate salt
  参考文献：
  名称：

  Synthesis of Filibuvir. Part I. Diastereoselective Preparation of a β-Hydroxy Alkynyl Oxazolidinone and Conversion to a 6,6-Disubstituted 2H-Pyranone

  摘要：

  This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate etiolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided beta-keto lactone 2.

  DOI：

  10.1021/op4002356
• 作为产物：
  描述：

  1-环戊基-2-丙炔-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲烷磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 生成 (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-1-(2,6-diethylpyridin-4-yl)-5-oxopent-1-yn-3-yl acetate
  参考文献：
  名称：

  Synthesis of Filibuvir. Part I. Diastereoselective Preparation of a β-Hydroxy Alkynyl Oxazolidinone and Conversion to a 6,6-Disubstituted 2H-Pyranone

  摘要：

  This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate etiolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided beta-keto lactone 2.

  DOI：

  10.1021/op4002356