benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-5-chloropentanoate | 133464-16-1

• 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-5-chloropentanoate
• 英文别名: benzyl 2(S)-[(tert-butoxycarbonyl)amino]-4-oxo-5-chloropentanoate；benzyl (2S)-5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxopentanoate
• CAS: 133464-16-1
• 化学式: C₁₇H₂₂ClNO₅
• 分子量: 355.818
• InChiKey: CMHQCVUMIOQQRI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-5-chloropentanoate 、 硫脲 以 丙酮 为溶剂， 反应 16.0h， 生成 α-N-BOC-β-(2'-amino-4'-thiazolyl)alanine benzyl ester hydrochloride
  参考文献：
  名称：

  Patt, William C.; Skeean, Richard W.; Steinbaugh, Bruce A., Synthetic Communications, 1990, vol. 20, # 20, p. 3097 - 3102

  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-5-chloropentanoate
  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

• 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：——
• 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.
• Patt, William C.; Skeean, Richard W.; Steinbaugh, Bruce A., Synthetic Communications, 1990, vol. 20, # 20, p. 3097 - 3102
  作者：Patt, William C.、Skeean, Richard W.、Steinbaugh, Bruce A.

  DOI：——

  日期：——