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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (5): 512-515. 上一篇    下一篇

研究论文

2-[1-(叔丁氧羰基氨基)乙基]噻唑-4-甲酸甲酯的合成

王晓季, 陈立功*, 李阳, 孟祎   

  1. 天津大学药物科学与技术学院 天津 300072
  • 收稿日期:2003-06-17 修回日期:2003-10-16 接受日期:2003-11-14 发布日期:2022-09-20

Synthesis of Methyl 2-(1-tert-Butoxycarbonylaminoethyl)thiazole-4-carboxylate

WANG, Xiao-Ji, CHEN, Li-Gong*, LI, Yang, MENG, Yi   

  1. School of Pharmaceutical Technology & Science, Tianjin University, Tianjin 300072
  • Received:2003-06-17 Revised:2003-10-16 Accepted:2003-11-14 Published:2022-09-20
  • Contact: *E-mail: lgchen@tju.edu.cn

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以(S)-丝氨酸和N-Boc-(S)-丙氨酸为原料,经酯化、偶合、TBS保护、硫化、脱保护、环合,脱氢等七步反应,合成了对人体肿瘤细胞KB和LoVo具有中等细胞毒性的天然环酯肽Obyanamide的噻唑结构片段2-[1-(叔丁氧羰基氨基)乙基]噻唑-4-甲酸甲酯,其ee值大于98%,总收率为21.4%.

关键词: (S)-丝氨酸, N-Boc-(S)-丙氨酸, 噻唑

Methyl 2-(1-tert-butoxycarbonylaminoethyl)thiazole-4-carboxylate, the chiral unit containing thiazole of a novel cyclic depsipeptide obyanamide which exhibited moderate cytotoxicity against KB andLoVo cells, was synthesized from (S)-serine and N-Boc-(S)-alanine in overall yield 21.4% through seven steps, including esterification, condensation, TBS protection, thionation, deprotection, cyclization and dehydrogenation. The ee value of the title chiral thiazole unit is up to 98%.

Key words: (S)-serine, N-Boc-(S)-alanine, thiazole