benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-hexanoate | 125942-84-9

• 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: benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-hexanoate
• 英文别名: benzyl 2(S)-[(tert-butoxycarbonyl)amino]-4-oxo-hexanoate；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoate
• CAS: 125942-84-9
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: QGECONDVZKBUDD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-hexanoate 生成 benzyl (2S)-4-oxo-2-[[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]hexanoate
  参考文献：
  名称：

  JACKSON, RICHARD F. W.;JAMES, KEITH;WYTHES, MARTIN J.;WOOD, ANTHONY, J. CHEM. SOC. CHEM. COMMUN.,(1989) N0, C. 644-645

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丝氨酸 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 锌铜偶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 49.0h， 生成 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-hexanoate
  参考文献：
  名称：

  Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine

  摘要：

  The organozinc reagent 13, prepared from the protected beta-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-alpha-amino acids 17 in 39-90% yield (13 examples). Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67% yield (11 examples). The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.

  DOI：

  10.1021/jo00038a030

文献信息

• A simple synthesis of γ and δ-keto α-amino acid derivatives
  作者：Norman Aubry、Raymond Plante、Robert Déziel

  DOI：10.1016/s0040-4039(00)97050-3

  日期：1990.1

  The γ and δ-keto α-amino acid derivatives 1a and 1b were prepared from L-aspartic and L-glutamic acid respectively via alkylation of the corresponding β-ketoesters 3a and 3b followed by subsequent ester cleavage and decarboxylation.

  γ和δ-酮α-氨基酸衍生物1a和1b分别由L-天冬氨酸和L-谷氨酸通过相应的β-酮酯3a和3b的烷基化，随后的酯裂解和脱羧而制备。
• A new direct method for the synthesis of enantiomerically pure protected α-amino acids
  作者：Richard F. W. Jackson、Keith James、Martin J. Wythes、Anthony Wood

  DOI：10.1039/c39890000644

  日期：——

  (2), prepared from the protected β-iodo alanine derivative (3) using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of (Ph3P)2PdCl2 to give high yields of enantiomerically pure protected γ-keto α-amino acids (4).

  在（Ph 3 P）2 PdCl 2的存在下，使用酰氯有效地酰化由保护的β-碘丙氨酸丙氨酸衍生物（3）制备的有机锌试剂（2），以高产率得到对映体纯的保护γ -酮基α-氨基酸（4）。
• JACKSON, RICHARD F. W.;JAMES, KEITH;WYTHES, MARTIN J.;WOOD, ANTHONY, J. CHEM. SOC. CHEM. COMMUN.,(1989) N0, C. 644-645
  作者：JACKSON, RICHARD F. W.、JAMES, KEITH、WYTHES, MARTIN J.、WOOD, ANTHONY

  DOI：——

  日期：——
• AUBRY, NORMAN;PLANTE, RAYMOND;DEZIEL, ROBERT, TETRAHEDRON LETT., 31,(1990) N4, C. 6311-6312
  作者：AUBRY, NORMAN、PLANTE, RAYMOND、DEZIEL, ROBERT

  DOI：——

  日期：——
• Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine
  作者：Richard F. W. Jackson、Neil Wishart、Anthony Wood、Keith James、Martin J. Wythes

  DOI：10.1021/jo00038a030

  日期：1992.6

  The organozinc reagent 13, prepared from the protected beta-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-alpha-amino acids 17 in 39-90% yield (13 examples). Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67% yield (11 examples). The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.