tert-butyl (4R)-4-((1E)-4,4-dimethyl-3,3-diphenyl-3-silapent-1-enyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 258351-75-6

• 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-((1E)-4,4-dimethyl-3,3-diphenyl-3-silapent-1-enyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[(E)-2-[tert-butyl(diphenyl)silyl]ethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 258351-75-6
• 化学式: C₂₈H₃₉NO₃Si
• 分子量: 465.708
• InChiKey: GULFFVUIUFPZOT-YVHXKWHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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-((1E)-4,4-dimethyl-3,3-diphenyl-3-silapent-1-enyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 Petroleum ether 为溶剂， 反应 7.0h， 以88%的产率得到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
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到tert-butyl (4R)-4-((1E)-4,4-dimethyl-3,3-diphenyl-3-silapent-1-enyl)-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

文献信息

• Silylcupration of (<i>R</i>)-2,2-Dimethyl-3-(<i>tert</i>-butoxycarbonyl)-4-ethynyloxazolidine:  A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids
  作者：Gianna Reginato、Alessandro Mordini、Michela Valacchi、Elena Grandini

  DOI：10.1021/jo991272r

  日期：1999.12.1

  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.