(2R,3R)-3-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]-2-(phenylmethoxymethyl)cyclobutane-1-carbaldehyde

• 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: (2R,3R)-3-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]-2-(phenylmethoxymethyl)cyclobutane-1-carbaldehyde
• 化学式: C₂₈H₂₇NO₄
• 分子量: 441.527
• InChiKey: WWDKUVWIWGURDS-QAWYLDNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]-2-(phenylmethoxymethyl)cyclobutane-1-carbaldehyde 在 palladium dihydroxide 咪唑 、 sodium tetrahydroborate 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 110.0 ℃ 、241.32 kPa 条件下， 反应 64.25h， 生成 4-N-[(1R,2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(phenylmethoxymethyl)cyclobutyl]-6-chloropyrimidine-4,5-diamine
  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：

  (4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-3-methylene-cyclobutyl)-4,5-diphenyl-oxazolidin-2-one 在 高氯酸 、 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 生成 (2R,3R)-3-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]-2-(phenylmethoxymethyl)cyclobutane-1-carbaldehyde 、 (4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-4-oxo-cyclopentyl)-4,5-diphenyl-oxazolidin-2-one 、 (4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-3-oxo-cyclopentyl)-4,5-diphenyl-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

文献信息

• Optically Active Cyclobutanone Chemistry:  Synthesis of (−)-Cyclobut-A and (±)-3‘-<i>Epi</i>-Cyclobut-A
  作者：Brian Brown、Louis S. Hegedus

  DOI：10.1021/jo9817063

  日期：1998.10.1

  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.