(4R,5S)-3-[(1R,2R,3S)-3-(hydroxymethyl)-2-(phenylmethoxymethyl)cyclobutyl]-4,5-diphenyl-1,3-oxazolidin-2-one | 215717-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5S)-3-[(1R,2R,3S)-3-(hydroxymethyl)-2-(phenylmethoxymethyl)cyclobutyl]-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 215717-11-6
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: JJZKPDLWUJJMGI-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(1R,2R,3S)-3-(hydroxymethyl)-2-(phenylmethoxymethyl)cyclobutyl]-4,5-diphenyl-1,3-oxazolidin-2-one 在 palladium dihydroxide 咪唑 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.75h， 生成 (1R,2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(phenylmethoxymethyl)cyclobutan-1-amine
  参考文献：
  名称：

  Optically Active Cyclobutanone Chemistry:  Synthesis of (−)-Cyclobut-A and (±)-3‘-Epi-Cyclobut-A

  摘要：

  The carbocyclic nucleoside analogues (-)-cyclobut-A and (+/-)-3'-epi-cyclobut-A were synthesized utilizing photolysis of the (benzyloxymethyl)(methoxy) chromium carbene complex 4 with optically active ene-carbamate 5 to produce the corresponding optically active alpha,alpha-disubstituted cyclobutanone 6. Stereoselective removal of the alpha-ethoxy group with inversion gave cyclobutanone 7, which was converted by existing methodology to the title compounds.

  DOI：

  10.1021/jo9817063
• 作为产物：
  描述：

  (2R,3R)-3-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]-2-(phenylmethoxymethyl)cyclobutane-1-carbaldehyde 在 sodium tetrahydroborate 、 sodium methylate 作用下， 生成 (4R,5S)-3-[(1R,2R,3S)-3-(hydroxymethyl)-2-(phenylmethoxymethyl)cyclobutyl]-4,5-diphenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Optically Active Cyclobutanone Chemistry:  Synthesis of (−)-Cyclobut-A and (±)-3‘-Epi-Cyclobut-A

  摘要：

  The carbocyclic nucleoside analogues (-)-cyclobut-A and (+/-)-3'-epi-cyclobut-A were synthesized utilizing photolysis of the (benzyloxymethyl)(methoxy) chromium carbene complex 4 with optically active ene-carbamate 5 to produce the corresponding optically active alpha,alpha-disubstituted cyclobutanone 6. Stereoselective removal of the alpha-ethoxy group with inversion gave cyclobutanone 7, which was converted by existing methodology to the title compounds.

  DOI：

  10.1021/jo9817063