(1R,2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(phenylmethoxymethyl)cyclobutan-1-amine | 215717-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(phenylmethoxymethyl)cyclobutan-1-amine
• CAS: 215717-15-0
• 化学式: C₁₉H₃₃NO₂Si
• 分子量: 335.562
• InChiKey: YAWJEROTAJPAMS-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 (1R,2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(phenylmethoxymethyl)cyclobutan-1-amine 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 23.0h， 以59%的产率得到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,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

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.