benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-pentanoate | 125942-83-8

• 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-pentanoate
• 英文别名: benzyl 2(S)-[(tert-butoxycarbonyl)amino]-4-oxo-pentanoate；N-[(1,1-Dimethylethoxy)carbonyl]-4-oxo-L-norvaline phenylmethyl ester；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxopentanoate
• CAS: 125942-83-8
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: XRIGGGWREKBODJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-pentanoate 生成 benzyl (2S)-4-oxo-2-[[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]pentanoate
  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-pentanoate
  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 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：——
• JACKSON, RICHARD F. W.;WOOD, ANTHONY;WYTHES, MERTIN J., SYNLETT.,(1990) N2, C. 735-736
  作者：JACKSON, RICHARD F. W.、WOOD, ANTHONY、WYTHES, MERTIN J.

  DOI：——

  日期：——
• US7371867B2
  申请人：——

  公开号：US7371867B2

  公开（公告）日：2008-05-13
• 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.