(R)-2-tert-Butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyl)-butyric acid | 258351-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-tert-Butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyl)-butyric acid
• 英文别名: (2R)-4-[tert-butyl(diphenyl)silyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 258351-79-0
• 化学式: C₂₅H₃₅NO₄Si
• 分子量: 441.643
• InChiKey: STOHUHHGWZZUKM-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-Butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyl)-butyric acid 、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以20%的产率得到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 chromium(VI) oxide 、 palladium on activated charcoal 氢气 、 高碘酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 、 Petroleum ether 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 14.5h， 生成 (R)-2-tert-Butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyl)-butyric acid
  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