(+)-N,O-bis(triisopropylsilyl)-L-tryptophan | 1211543-67-7

• 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: (+)-N,O-bis(triisopropylsilyl)-L-tryptophan
• 英文别名: tri(propan-2-yl)silyl (2S)-3-(1H-indol-3-yl)-2-[tri(propan-2-yl)silylamino]propanoate
• CAS: 1211543-67-7
• 化学式: C₂₉H₅₂N₂O₂Si₂
• 分子量: 516.915
• InChiKey: SWZNPEQIAMEFGS-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 (+)-N,O-bis(triisopropylsilyl)-L-tryptophan 在 叔丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 0.25h， 以93%的产率得到(+)-N,O-bis(triisopropylsilyl)-N(1)-(triethylsilyl)-(S)-tryptophan
  参考文献：
  名称：

  Selective Triisopropylsilylation of α-Amino Acids: Protection without Racemization

  摘要：

  The mono-, di- and trisilylation of alpha-amino acids with TIPSOTf is described. Treatment of the alpha-amino acids, proline and tryptophan with TIPSOTf in MeCN provides a quantitative yield of the corresponding ammonium salts of the O-TIPS esters (4). Employing two (2) equivalents of TIPSOTf/EDIPA produces N,O-bis-TIPS amino acid derivatives (2) without racemization as stable compounds (73-87%, 13 examples). Three (3) equivalents of this silylation mixture produces the corresponding tris-TIPS derivatives 6 (62-88%, 6 examples) from amino acids which contain protic functionality in their side chain. While this trisilylation procedure is ineffective for tryptophan, the N,O-bis-TIPS derivative 2m is easily prepared through this method, and the third silylation is achieved without racemization employing t-BuLi/R3SiX producing N-1-SiR3-N,O-bis-TIPS tryptophans (51-97%, 4 examples).

  DOI：

  10.3987/com-09-s(s)37
• 作为产物：
  描述：

  三异丙基硅基三氟甲磺酸酯 、 L-色氨酸 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(+)-N,O-bis(triisopropylsilyl)-L-tryptophan
  参考文献：
  名称：

  Selective Triisopropylsilylation of α-Amino Acids: Protection without Racemization

  摘要：

  The mono-, di- and trisilylation of alpha-amino acids with TIPSOTf is described. Treatment of the alpha-amino acids, proline and tryptophan with TIPSOTf in MeCN provides a quantitative yield of the corresponding ammonium salts of the O-TIPS esters (4). Employing two (2) equivalents of TIPSOTf/EDIPA produces N,O-bis-TIPS amino acid derivatives (2) without racemization as stable compounds (73-87%, 13 examples). Three (3) equivalents of this silylation mixture produces the corresponding tris-TIPS derivatives 6 (62-88%, 6 examples) from amino acids which contain protic functionality in their side chain. While this trisilylation procedure is ineffective for tryptophan, the N,O-bis-TIPS derivative 2m is easily prepared through this method, and the third silylation is achieved without racemization employing t-BuLi/R3SiX producing N-1-SiR3-N,O-bis-TIPS tryptophans (51-97%, 4 examples).

  DOI：

  10.3987/com-09-s(s)37