(R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid tert-butyl ester | 1204514-50-0

• 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: (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-3-hydroxy-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1204514-50-0
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: AERYVCCJUIXOJF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid tert-butyl ester 在 吡啶 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 以67.2%的产率得到(R)-3-(tert-butoxycarbonyl)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2-oxide
  参考文献：
  名称：

  Synthesis, Radiolabeling, and Biological Evaluation of (R)- and (S)-2-Amino-3-[¹⁸F]Fluoro-2-Methylpropanoic Acid (FAMP) and (R)- and (S)-3-[¹⁸F]Fluoro-2-Methyl-2-N-(Methylamino)propanoic Acid (NMeFAMP) as Potential PET Radioligands for Imaging Brain Tumors

  摘要：

  The non-natural amino acids (R)- and (S)-2-amino-3-fluoro-2-methylpropanoic acid 5 and (R)- and (S)-3-fluoro-2-methyl-2-N-(methylamino)propanoic acid 8 were synthesized in shorter reaction sequences than in the original report starting from enantiomerically pure (S)- and (R)-alpha-methyl-serine, respectively. The reaction sequence provided the Cyclic sulfamidate precursors for radiosynthesis or (R)- and (S)-[F-18]5 and (R)- and (S)-[F-18]8 in fewer steps than in the original report. (R)- and (S)-[F-18]5 and (R)- and (S)-[F-18]8 were synthesized by no-carrier-added nucleophilic [F-18]fluorination in 52-66% decay-corrected yields with radiochemical purity over 99%. The cell assays showed that all four compounds were substrates for amino acid transport and enter 9L rat gliosarcoma cells in vitro at least in part by system A amino acid transport, The biodistribution Studies demonstrated that in vivo tumor to normal brain ratios for all compounds were high with ratios of 20:1 to 115:1 in rats with intracranial 9L tumors. The (R)-enantiomers of [F-18]5 and [F-18]8 demonstrated higher tumor uptake in vivo compared to the (S)-enantiomers.

  DOI：

  10.1021/jm900556s
• 作为产物：
  描述：

  N-Boc-2-甲基-D-丝氨酸 、 N,N-二甲基甲酰胺二叔丁基缩醛 以 甲苯 为溶剂， 以290 mg的产率得到(R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, Radiolabeling, and Biological Evaluation of (R)- and (S)-2-Amino-3-[¹⁸F]Fluoro-2-Methylpropanoic Acid (FAMP) and (R)- and (S)-3-[¹⁸F]Fluoro-2-Methyl-2-N-(Methylamino)propanoic Acid (NMeFAMP) as Potential PET Radioligands for Imaging Brain Tumors

  摘要：

  The non-natural amino acids (R)- and (S)-2-amino-3-fluoro-2-methylpropanoic acid 5 and (R)- and (S)-3-fluoro-2-methyl-2-N-(methylamino)propanoic acid 8 were synthesized in shorter reaction sequences than in the original report starting from enantiomerically pure (S)- and (R)-alpha-methyl-serine, respectively. The reaction sequence provided the Cyclic sulfamidate precursors for radiosynthesis or (R)- and (S)-[F-18]5 and (R)- and (S)-[F-18]8 in fewer steps than in the original report. (R)- and (S)-[F-18]5 and (R)- and (S)-[F-18]8 were synthesized by no-carrier-added nucleophilic [F-18]fluorination in 52-66% decay-corrected yields with radiochemical purity over 99%. The cell assays showed that all four compounds were substrates for amino acid transport and enter 9L rat gliosarcoma cells in vitro at least in part by system A amino acid transport, The biodistribution Studies demonstrated that in vivo tumor to normal brain ratios for all compounds were high with ratios of 20:1 to 115:1 in rats with intracranial 9L tumors. The (R)-enantiomers of [F-18]5 and [F-18]8 demonstrated higher tumor uptake in vivo compared to the (S)-enantiomers.

  DOI：

  10.1021/jm900556s