N-[(1R)-1-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2-hydroxyethyl](tert-butoxy)carboxamide | 258351-77-8

• 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: N-[(1R)-1-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2-hydroxyethyl](tert-butoxy)carboxamide
• 英文别名: tert-butyl N-[(2R)-4-[tert-butyl(diphenyl)silyl]-1-hydroxybutan-2-yl]carbamate
• CAS: 258351-77-8
• 化学式: C₂₅H₃₇NO₃Si
• 分子量: 427.659
• InChiKey: WQKSCCUJOAJOIA-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2-hydroxyethyl](tert-butoxy)carboxamide 在 chromium(VI) oxide 高碘酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以70%的产率得到(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
• 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 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 Petroleum ether 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 N-[(1R)-1-(4,4-dimethyl-3,3-diphenyl-3-silapentyl)-2-hydroxyethyl](tert-butoxy)carboxamide
  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.