(S)-3-((3S,4S)-4-Benzylamino-3-methyl-2-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one | 140705-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-((3S,4S)-4-Benzylamino-3-methyl-2-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one
• CAS: 140705-88-0
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: BZKXHDFSDUSSPN-OPYAIIAOSA-N

反应信息

• 作为反应物：
  描述：

  (S)-3-((3S,4S)-4-Benzylamino-3-methyl-2-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1S,5S,8aS)-2-Benzyl-1-hydroxymethyl-8a-methyl-5-phenyl-tetrahydro-imidazo[5,1-c][1,4]oxazine-3,8-dione
  参考文献：
  名称：

  Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

  摘要：

  Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

  DOI：

  10.1016/s0040-4039(00)91567-3
• 作为产物：
  描述：

  (S)-3-((2S,3S)-2-Hydroxymethyl-3-methyl-4-oxo-1-phenyl-azetidin-3-yl)-4-phenyl-oxazolidin-2-one 在 硫酸 作用下， 以 正丁醇 为溶剂， 以100%的产率得到(S)-3-((3S,4S)-4-Benzylamino-3-methyl-2-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

  摘要：

  Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

  DOI：

  10.1016/s0040-4039(00)91567-3