(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoate | 1204514-49-7

• 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: (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoate
• 英文别名: (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid tert-butyl ester；tert-butyl (2S)-3-hydroxy-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1204514-49-7
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: AERYVCCJUIXOJF-ZDUSSCGKSA-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：

  (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoate 在 吡啶 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 以95.3%的产率得到(S)-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-L-丝氨酸 、 N,N-二甲基甲酰胺二叔丁基缩醛 以 甲苯 为溶剂， 以267 mg的产率得到(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoate
  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

文献信息

• Synthesis and Biological Evaluation of (<i>S</i>)-Amino-2-methyl-4-[⁷⁶Br]bromo-3-(<i>E</i>)-butenoic Acid (BrVAIB) for Brain Tumor Imaging
  作者：Jennifer L. Bartels、Chaofeng Huang、Aixiao Li、Liya Yuan、Keith Rich、Jonathan McConathy、Suzanne E. Lapi

  DOI：10.1021/acs.jmedchem.5b01035

  日期：2015.11.12

  The novel compound, (S)-amino-2-methyl-4-[Br-76]-bromo-3-(E)-butenoic acid (BrVAIB, [Br-76]5), was characterized against the known system A tracer, IVAIB ( [I-123]8). [Br-76]5 was prepared in a 51% +/- 19% radiochemical yield with high radiochemical purity (>= 98%). The biological properties of [Br-76]5 were compared with those of [I-123]8. Results showed that [Br-76]5 undergoes mixed amino acid transport by system A and system L transport, while [I-123]8 had less uptake by system L. [Br-76]5 demonstrated higher uptake than [I-123]8 in DBT tumors 1 h after injection (3.7 +/- 0.4% ID/g vs 1.5 +/- 0.3% ID/g) and also showed higher uptake vs [I-123]8 in normal brain. Small animal PET studies with [Br-76]5 demonstrated good tumor visualization of intracranial DBTs up to 24 h with clearance from normal tissues. These results indicate that [Br-76]5 is a promising PET tracer for brain tumor imaging and lead compound for a mixed system A and system L transport substrate.
• Synthesis, Radiolabeling, and Biological Evaluation of (<i>R</i>)- and (<i>S</i>)-2-Amino-3-[¹⁸F]Fluoro-2-Methylpropanoic Acid (FAMP) and (<i>R</i>)- and (<i>S</i>)-3-[¹⁸F]Fluoro-2-Methyl-2-<i>N</i>-(Methylamino)propanoic Acid (<i>N</i>MeFAMP) as Potential PET Radioligands for Imaging Brain Tumors
  作者：Weiping Yu、Jonathan McConathy、Larry Williams、Vernon M. Camp、Eugene J. Malveaux、Zhaobin Zhang、Jeffrey J. Olson、Mark M. Goodman

  DOI：10.1021/jm900556s

  日期：2010.1.28

  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.