(2'S)-2-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-6-methyl-4-phenylpyridine-3,5-dicarboxylic acid di-tert-butyl ester | 596828-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2'S)-2-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-6-methyl-4-phenylpyridine-3,5-dicarboxylic acid di-tert-butyl ester
• 英文别名: (2S)-3-[6-methyl-3,5-bis[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylpyridin-2-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 596828-20-5
• 化学式: C₃₀H₄₀N₂O₈
• 分子量: 556.656
• InChiKey: CLUGZBVIMMUBIY-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2'S)-2-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-6-methyl-4-phenylpyridine-3,5-dicarboxylic acid di-tert-butyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.08h， 生成 (2'S,2''R)-2-[2'-methoxycarbonyl-2'-(3'',3'',3''-trifluoro-2''-methoxy-2''-phenylpropionylamino)ethyl]-6-methyl-4-phenylpyrdine-3,5-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Model Studies toward the Synthesis of Dihydropyrimidinyl and Pyridyl α-Amino Acids via Three-Component Biginelli and Hantzsch Cyclocondensations

  摘要：

  A novel and versatile strategy for the synthesis of heterocyclic a-amino acids has been described. The use of components (aldehyde or beta-ketoester) bearing a masked glycinyl moiety in Biginelli and Hantzsch cyclocondensations allowed access to the 4-dihydropyrimidinyl-alpha-glycines, 4-dihydropyrimidinyl-alpha-alanines, 4-pyridyl-alpha-alanines, and 2-pyridyl-alpha-alanines classes. Dihydropyrimidinyl-amino acids were obtained as a mixture of diastereoisomers due to the formation of the stereocenter at C4 of the dibydropyrimidinone ring. Individual stereoisomers were isolated as pure compounds and their structures were assigned with the aid of X-ray crystallography and chiroptical properties. The enantiomeric purity of a representative selection of the above amino acids was greater than 96% as verified by derivatization to the corresponding Mosher's amides and subsequent H-1 and F-19 NMR spectroscopy. Incorporation of the 4-pyridyl-alpha-alanine derivative into a peptide chain is also described.

  DOI：

  10.1021/jo0342830
• 作为产物：
  描述：

  (2S)-2-tert-butoxycarbonylamino-4-oxo-hexane-dioic acid 1-benzyl ester 6-tert-butyl ester 在 palladium dihydroxide 氢气 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 26.25h， 生成 (2'S)-2-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-6-methyl-4-phenylpyridine-3,5-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  多组分Hantzsch环缩合反应作为高度官能化的2-和4-二氢吡啶基丙氨酸，2-和4-吡啶基丙氨酸及其N氧化物的途径：通过聚合物辅助溶液相法制备

  摘要：

  通过一锅式热Hantzsch型环缩合反应，已经开发出了一种改进且有效的进入高度官能化的β-（2-吡啶基）-和β-（4-吡啶基）丙氨酸以及相应的1,4-二氢和N-氧化物衍生物的方法。醛-酮酸酯-烯胺系统，其中一种试剂（醛或酮酸酯）带有未掩盖但受保护的手性甘氨酰部分。因此，将N- Boc - O-苄基天冬氨酸β-醛，乙酰乙酸酯和氨基巴豆酸酯偶联，得到四取代的β-（4-二氢吡啶基）丙氨酸（75％收率）。这些产物之一几乎被定量转化为β-（4-吡啶基）丙氨酸衍生物，后者被氧化成相应的N-氧化物。通过与（S）-苯丙氨酸偶合，将这些对映体纯的（Mosher酰胺分析）杂环α-氨基酸中的每一个掺入三肽中。以类似的方式，通过苯并甲醛，氨基巴豆酸酯和乙酰乙酸酯与苯甲醛一起经Hantzsch环缩合反应制备四取代的β-（2-二氢吡啶基）丙氨酸，β-（2-吡啶基）丙氨酸和β-（1-氧化-2-吡啶基）丙氨酸。N- Boc-

  DOI：

  10.1016/j.tet.2004.01.011

文献信息

• Model Studies toward the Synthesis of Dihydropyrimidinyl and Pyridyl α-Amino Acids via Three-Component Biginelli and Hantzsch Cyclocondensations
  作者：Alessandro Dondoni、Alessandro Massi、Erik Minghini、Simona Sabbatini、Valerio Bertolasi

  DOI：10.1021/jo0342830

  日期：2003.8.1

  A novel and versatile strategy for the synthesis of heterocyclic a-amino acids has been described. The use of components (aldehyde or beta-ketoester) bearing a masked glycinyl moiety in Biginelli and Hantzsch cyclocondensations allowed access to the 4-dihydropyrimidinyl-alpha-glycines, 4-dihydropyrimidinyl-alpha-alanines, 4-pyridyl-alpha-alanines, and 2-pyridyl-alpha-alanines classes. Dihydropyrimidinyl-amino acids were obtained as a mixture of diastereoisomers due to the formation of the stereocenter at C4 of the dibydropyrimidinone ring. Individual stereoisomers were isolated as pure compounds and their structures were assigned with the aid of X-ray crystallography and chiroptical properties. The enantiomeric purity of a representative selection of the above amino acids was greater than 96% as verified by derivatization to the corresponding Mosher's amides and subsequent H-1 and F-19 NMR spectroscopy. Incorporation of the 4-pyridyl-alpha-alanine derivative into a peptide chain is also described.
• Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides: preparation via a polymer-assisted solution-phase approach
  作者：Alessandro Dondoni、Alessandro Massi、Erik Minghini、Valerio Bertolasi

  DOI：10.1016/j.tet.2004.01.011

  日期：2004.3

  incorporated into a tripeptide by coupling with (S)-phenylalanine. In a similar way tetrasubstituted β-(2-dihydropyridyl)alanine, β-(2-pyridyl)alanine and β-(1-oxido-2-pyridyl)alanine were prepared via Hantzsch cyclocondensation reaction using benzaldehyde, aminocrotonate, and acetoacetate carrying the N-Boc-O-benzyl glycinate moiety. It was shown that the work up of the reaction mixtures derived from the cyclocondensation

  通过一锅式热Hantzsch型环缩合反应，已经开发出了一种改进且有效的进入高度官能化的β-（2-吡啶基）-和β-（4-吡啶基）丙氨酸以及相应的1,4-二氢和N-氧化物衍生物的方法。醛-酮酸酯-烯胺系统，其中一种试剂（醛或酮酸酯）带有未掩盖但受保护的手性甘氨酰部分。因此，将N- Boc - O-苄基天冬氨酸β-醛，乙酰乙酸酯和氨基巴豆酸酯偶联，得到四取代的β-（4-二氢吡啶基）丙氨酸（75％收率）。这些产物之一几乎被定量转化为β-（4-吡啶基）丙氨酸衍生物，后者被氧化成相应的N-氧化物。通过与（S）-苯丙氨酸偶合，将这些对映体纯的（Mosher酰胺分析）杂环α-氨基酸中的每一个掺入三肽中。以类似的方式，通过苯并甲醛，氨基巴豆酸酯和乙酰乙酸酯与苯甲醛一起经Hantzsch环缩合反应制备四取代的β-（2-二氢吡啶基）丙氨酸，β-（2-吡啶基）丙氨酸和β-（1-氧化-2-吡啶基）丙氨酸。N- Boc-