benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(2'-pyridyl)propionate | 127977-27-9

• 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>-3-(2'-pyridyl)propionate
• 英文别名: benzyl 2(S)-[(tert-butoxycarbonyl)amino]-3-(2'-pyridyl)propionate；(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyridin-2-ylpropanoate
• CAS: 127977-27-9
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: SSJNCSQBKHQLTR-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.5
• 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>-3-(2'-pyridyl)propionate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 以to provide (S)-benzyl 2-amino-3-(pyridin-2-yl)propanoate TFA salt (quant. yield) as a yellow oil的产率得到(S)-benzyl 2-amino-3-(pyridin-2-yl)propanoate TFA salt
  参考文献：
  名称：

  TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS

  摘要：

  本文提供了三肽环氧酮蛋白酶抑制剂及其制备方法、相关药物组合物和使用方法。例如，本文提供了式（X）的化合物及其药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗包括炎症和神经退行性疾病在内的疾病。

  公开号：

  US20140336106A1
• 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>-3-(2'-pyridyl)propionate
  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

• TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS
  申请人：Onyx Therapeutics, Inc.

  公开号：US20140336106A1

  公开（公告）日：2014-11-13

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂及其制备方法、相关药物组合物和使用方法。例如，本文提供了式（X）的化合物及其药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗包括炎症和神经退行性疾病在内的疾病。
• Synthesis of enantiomerically pure protected β-aryl alanines
  作者：Richard F.W. Jackson、Martin J. Wythes、Anthony Wood

  DOI：10.1016/s0040-4039(01)93511-7

  日期：1989.1
• 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.
• Tripeptide epoxy ketone protease inhibitors
  申请人：Onyx Therapeutics, Inc.

  公开号：US09434761B2

  公开（公告）日：2016-09-06

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂，其制备方法，相关药物组合物及其使用方法。例如，本文提供了X式化合物及其药学上可接受的盐和组合物。本文提供的化合物和组合物可用于治疗炎症和神经退行性疾病等疾病。