tert-butyl (4R)-4-(3,3-dimethyl-3-silabutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 219870-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4R)-4-(3,3-dimethyl-3-silabutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-2,2-dimethyl-4-(2-trimethylsilylethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 219870-27-6
• 化学式: C₁₅H₃₁NO₃Si
• 分子量: 301.502
• InChiKey: KAGYWPPVUHAKRE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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-(3,3-dimethyl-3-silabutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-[(1R)-1-(3,3-dimethyl-3-silabutyl)-2-hydroxyethyl](tert-butoxy)carboxamide
  参考文献：
  名称：

  A stereoselective approach to the synthesis of γ-silylated amino acids

  摘要：

  The synthesis of enantiomerically enriched silicon containing amino acids is described. Silylcupration of 2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine, easily derived from serine aldehyde, afforded regio- and stereoselectively gamma-silylated ethenyloxazolidines of (E)-geometry as useful precursors of saturated and unsaturated gamma-silylated amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02120-0
• 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 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 tert-butyl (4R)-4-(3,3-dimethyl-3-silabutyl)-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

• A stereoselective approach to the synthesis of γ-silylated amino acids
  作者：Gianna Reginato、Alessandro Mordini、Michela Valacchi

  DOI：10.1016/s0040-4039(98)02120-0

  日期：1998.12

  The synthesis of enantiomerically enriched silicon containing amino acids is described. Silylcupration of 2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine, easily derived from serine aldehyde, afforded regio- and stereoselectively gamma-silylated ethenyloxazolidines of (E)-geometry as useful precursors of saturated and unsaturated gamma-silylated amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.