tert-butyl (4R)-4-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 258351-76-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl (4R)-4-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[2-[tert-butyl(diphenyl)silyl]ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 258351-76-7
• 化学式: C₂₈H₄₁NO₃Si
• 分子量: 467.724
• InChiKey: AJDQCTWKQVGPEW-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 chromium(VI) oxide potassium hydrogencarbonate 、 高碘酸 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 methyl (2R)-2-[(tert-butoxy)carbonylamino]-6,6-dimethyl-5,5-diphenyl-5-silaheptanoate
  参考文献：
  名称：

  Silylcupration of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids

  摘要：

  Enantioselective synthesis of gamma-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final-compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, beta,gamma-unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.

  DOI：

  10.1021/jo991272r
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 Petroleum ether 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 tert-butyl (4R)-4-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Silylcupration of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids

  摘要：

  Enantioselective synthesis of gamma-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final-compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, beta,gamma-unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.

  DOI：

  10.1021/jo991272r