Tang G H, Zhang L, Tang X L, Wang Y X, Yin D Z
Radiopharmaceutical Research Centre, Shanghai Institute of Nuclear Research, Chinese Academy of Sciences, Shanghai 201800, China.
Yao Xue Xue Bao. 2001 Oct;36(10):739-42.
To study the synthesis and determination for enantiomeric purity of 6-fluoro-L-3, 4-dihydroxyphenylalanine (6-fluoro-L-DOPA, 6-FDOPA).
2-(2-Fluoro-4, 5-dimethoxybenzyl)-N-(diphenylmethylene) glycine tert-butyl ester (8), a new compound, was synthesized from the starting material nitroveratraldehyde via the nucleophilic displacement, reductive iodination, and chiral catalytic phase-transfer alkylation, and 6-FDOPA was prepared from hydrolysis of 8. The enantiomeric purity of 6-FDOPA was determined by HPLC method using a chiral mobil phase and reversed-phase C18 column.
The total time of synthesis was less than 90 min, the overall chemical yield from potassium fluoride was about 33%, and the enantiomeric purity was above 95%.
Large scale production of 6-FDOPA and automatic synthesis of 6-[18F]fluoro-L-DOPA with excellent chemical and entiomeric purity are available. The practical technique was provided for the radiochemical synthesis and entiomeric purity of 6-[18F]fluoro-L-DOPA.
研究6-氟-L-3,4-二羟基苯丙氨酸（6-氟-L-多巴，6-FDOPA）的合成及对映体纯度的测定。
以藜芦醛为起始原料，经亲核取代、还原碘化及手性催化相转移烷基化反应合成了新化合物2-(2-氟-4,5-二甲氧基苄基)-N-(二苯基亚甲基)甘氨酸叔丁酯（8），并通过8的水解反应制备了6-FDOPA。采用手性流动相和反相C18柱的高效液相色谱法测定6-FDOPA的对映体纯度。
合成总时间少于90分钟，以氟化钾计的总化学产率约为33%，对映体纯度高于95%。
可实现6-FDOPA的大规模生产以及具有优异化学和对映体纯度的6-[18F]氟-L-多巴的自动合成。为6-[18F]氟-L-多巴的放射化学合成及对映体纯度提供了实用技术。
