(2S,5'S)-N-tert-butoxycarbonyl-2-amino-2-(3'-benzyloxy-4',5'-dihydroisoxazol-5'-yl)acetic acid | 1020071-25-3

• 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: (2S,5'S)-N-tert-butoxycarbonyl-2-amino-2-(3'-benzyloxy-4',5'-dihydroisoxazol-5'-yl)acetic acid
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(5S)-3-phenylmethoxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
• CAS: 1020071-25-3
• 化学式: C₁₇H₂₂N₂O₆
• 分子量: 350.371
• InChiKey: QYVGIZZURRTQST-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5'S)-N-tert-butoxycarbonyl-2-amino-2-(3'-benzyloxy-4',5'-dihydroisoxazol-5'-yl)acetic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

  摘要：

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.

  DOI：

  10.1021/jm701394a
• 作为产物：
  描述：

  (2R,5'S)-N-tert-butoxycarbonyl-2-amino-2-(3'-benzyloxy-4',5'-dihydroisoxazol-5'-yl)ethanol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,5'S)-N-tert-butoxycarbonyl-2-amino-2-(3'-benzyloxy-4',5'-dihydroisoxazol-5'-yl)acetic acid
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

  摘要：

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.

  DOI：

  10.1021/jm701394a

文献信息

• Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid
  作者：Andrea Pinto、Paola Conti、Marco De Amici、Lucia Tamborini、Ulf Madsen、Birgitte Nielsen、Thomas Christesen、Hans Bräuner-Osborne、Carlo De Micheli

  DOI：10.1021/jm701394a

  日期：2008.4.1

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.