ASYMMETRIC-SYNTHESIS OF L-2-AMINO[3-C-11]BUTYRIC ACID, L-[3-C-11]NORVALINE AND L-[3-C-11]VALINE
ASYMMETRIC-SYNTHESIS OF L-2-AMINO[3-C-11]BUTYRIC ACID, L-[3-C-11]NORVALINE AND L-[3-C-11]VALINE
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DOI：
10.3891/acta.chem.scand.41b-0511
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发表时间：
1987-08-01
期刊：
影响因子：
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通讯作者：
LANGSTROM, B
中科院分区：
文献类型：
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作者：
ANTONI, G;LANGSTROM, B
短寿命放射性核素~（11）C（t1/2 = 20.4 min）已用于L-2-氨基[3-~（11）C]丁酸、L-[3-~（13）C]-正缬氨酸和L-[3-~（13）C]缬氨酸的不对称合成。在无水条件下，在四氢呋喃/1，3-二甲基-3，4，5，6-四氢-2-嘧啶酮中，以锂化的2，2，6，6-四甲基哌啶为碱，使用在一锅反应器中由[11 C]二氧化碳制备的适当的1C-烷基碘，通过[（+）-2-羟基庚基-3-亚基]甘氨酸叔丁酯的烷基化进行合成。除去保护基后，得到的-[3- 11 C]氨基酸的对映体过量为80-82%，放射化学产率为9-25%，衰变校正和计算的基础上的[11 C]二氧化碳在合成开始时在50-55分钟内。
The short-lived radionuclide 11C (t1/2 = 20.4 min) has been used in the asymmetric synthesis of L-2-amino[3-11C]butyric acid, L-[3-13C]-norvaline and L-[3-13C]valine. The syntheses were performed by alkylation of [(+)-2-hydroxypinanyl-3-idene]glycine tert-butyl ester under anhydrous conditions in tetrahydrofuran/1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone with lithiated 2,2,6,6-tetramethylpiperidine as base, using the appropriate 1C-alkyl iodides prepared in a one-pot reactor from [11C]carbon dioxide. Following removal of the protecting groups, the -[3-11C]amino acids were obtained in 80-82% enantiomeric excess and in 9-25% radiochemical yields, decay corrected and calculated on the basis of the amount of [11C]carbon dioxide at the start of the syntheses within 50-55 min.