(R)-3,4-dimethyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide | 1204514-60-2

• 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)-3,4-dimethyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide
• 英文别名: tert-butyl (4R)-3,4-dimethyl-2,2-dioxooxathiazolidine-4-carboxylate
• CAS: 1204514-60-2
• 化学式: C₉H₁₇NO₅S
• 分子量: 251.304
• InChiKey: PUIYUPMBLHKYCG-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3,4-dimethyl-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide 在 potassium fluoride 、 乙腈 、 盐酸 作用下， 生成
  参考文献：
  名称：

  手性环状氨基磺酸酯前体的开环亲核11C氰化反应合成l [[4-11C]天冬酰胺

  摘要：

  合成方便的，快速的方法以合成放射性标记的，对映体纯的氨基酸（AAs）作为潜在的正电子发射断层扫描（PET）成像剂，以绘制活体生物的各种生化转变仍然是一个挑战。鉴于碳11的半衰期较短（11 C，t 1/2 = 20.4分钟），对于碳11标记的AA的合成尤其如此。制备对映体纯的11 C标记的l的简便合成途径用部分保护的丝氨酸为原料开发了天冬酰胺，并进行了四步转化，提供了手性五元环氨基磺酸盐作为放射性标记前体。X射线晶体学证实了其结构和绝对构型。利用[ 11 C]的氰化物亲核开环反应，接着通过选择性酸性水解和脱保护，对映体纯升- [4- 11 C]天冬酰胺的合成。反应参数的进一步优化，包括碱金属离子源，溶剂，酸成分，反应温度和反应时间，用于合成可靠两步法升- [4- 11 C]天冬酰胺被提出：45±3分钟内（n从轰击结束= 5，合成了所需的对映体纯产物，其初始亲核氰化产率为69±4％（n = 5），两步放射化学总产率为53±2％（n

  DOI：

  10.1002/chem.201801029
• 作为产物：
  描述：

  (R)-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66.4%的产率得到(R)-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

文献信息

• Synthesis of <scp>l</scp> -[4-¹¹ C]Asparagine by Ring-Opening Nucleophilic ¹¹ C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor
  作者：Youwen Xu、Aylin Sibel Cankaya、Ruma Hoque、So Jeong Lee、Colleen Shea、Lena Kersting、Michael Schueller、Joanna S. Fowler、David Szalda、David Alexoff、Barbara Riehl、Tassilo Gleede、Richard A. Ferrieri、Wenchao Qu

  DOI：10.1002/chem.201801029

  日期：2018.5.7

  by X‐ray crystallography. Utilizing a [11C]cyanide nucleophilic ring opening reaction followed by selective acidic hydrolysis and deprotection, enantiomerically pure l‐[4‐11C]asparagine was synthesized. Further optimization of reaction parameters, including base, metal ion source, solvent, acid component, reaction temperature and reaction time, a reliable two‐step method for synthesizing l‐[4‐11C]asparagine

  合成方便的，快速的方法以合成放射性标记的，对映体纯的氨基酸（AAs）作为潜在的正电子发射断层扫描（PET）成像剂，以绘制活体生物的各种生化转变仍然是一个挑战。鉴于碳11的半衰期较短（11 C，t 1/2 = 20.4分钟），对于碳11标记的AA的合成尤其如此。制备对映体纯的11 C标记的l的简便合成途径用部分保护的丝氨酸为原料开发了天冬酰胺，并进行了四步转化，提供了手性五元环氨基磺酸盐作为放射性标记前体。X射线晶体学证实了其结构和绝对构型。利用[ 11 C]的氰化物亲核开环反应，接着通过选择性酸性水解和脱保护，对映体纯升- [4- 11 C]天冬酰胺的合成。反应参数的进一步优化，包括碱金属离子源，溶剂，酸成分，反应温度和反应时间，用于合成可靠两步法升- [4- 11 C]天冬酰胺被提出：45±3分钟内（n从轰击结束= 5，合成了所需的对映体纯产物，其初始亲核氰化产率为69±4％（n = 5），两步放射化学总产率为53±2％（n
• 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.