(4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-2-ethoxy-3-oxo-cyclobutyl)-4,5-diphenyl-oxazolidin-2-one | 210904-63-5

• 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)-2-Benzyloxymethyl-2-ethoxy-3-oxo-cyclobutyl)-4,5-diphenyl-oxazolidin-2-one
• 英文别名: (4R,5S)-3-[(1R,2R)-2-ethoxy-3-oxo-2-(phenylmethoxymethyl)cyclobutyl]-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 210904-63-5
• 化学式: C₂₉H₂₉NO₅
• 分子量: 471.553
• InChiKey: FGKIPJJZCFTXTO-ZLMHUZRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-2-ethoxy-3-oxo-cyclobutyl)-4,5-diphenyl-oxazolidin-2-one 在 samarium diiodide 、 硼烷四氢呋喃络合物 、 草酰氯 、 四氯化钛 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 19.87h， 生成 (1R,2R,3R)-2-Benzyloxymethyl-3-((4R,5S)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-cyclobutanecarbaldehyde
  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)-4,5-diphenyl-3-vinyl-2-oxazolidinone 、 alkaline earth salt of/the/ methylsulfuric acid 在 一氧化碳 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 生成 (4R,5S)-3-((1R,2R)-2-Benzyloxymethyl-2-ethoxy-3-oxo-cyclobutyl)-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

• Photochemical Ring Expansion of α-Alkoxycyclobutanones to 2-Acetoxy-5-alkoxytetrahydrofurans:  Nucleophilic Reactions at the 2-Position
  作者：Gisela Umbricht、Melissa D. Hellman、Louis S. Hegedus

  DOI：10.1021/jo980429x

  日期：1998.7.1

  Photolysis of cyclobutanones in:the presence of acetic acid produced 2-acetoxy-5-alkoxytetrahydrofurans regiospecifically and with retention of configuration at the migrating alpha-position. The acetoxy group was replaced by nucleophiles such as allylsilane, trimethylsilyl azide, diethylaluminum cyanide, and silylated thymine in the presence of Lewis acids.