(S)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide | 1204514-57-7

• 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)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide
• 英文别名: tert-butyl (4S)-4-methyl-2,2-dioxooxathiazolidine-4-carboxylate
• CAS: 1204514-57-7
• 化学式: C₈H₁₅NO₅S
• 分子量: 237.277
• InChiKey: FRZAYCYLOLHISL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide 在 sodium hydride 、 硫酸二甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以56.9%的产率得到(S)-3,4-dimethyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide
  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：

  (S)-3-(tert-butoxycarbonyl)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide 在 甲烷磺酸 作用下， 以 醋酸叔丁酯 、 二氯甲烷 为溶剂， 以56.5%的产率得到(S)-4-methyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide
  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, 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.