A general approach to l-tyrosine porphyrins |
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Authors: | Hong ChenXue-Bin Shao Xi-Kui JiangZhan-Ting Li |
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Affiliation: | Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China |
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Abstract: | A novel and general approach has been developed to prepare l-tyrosine-containing porphyrins. The key intermediates, 2-tert-butoxycarbonylamino-3-(3-formyl-4-hexyloxy-phenyl)-propionic acid hexyl ester and 2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester, were prepared by the Reimer-Tiemann reaction of Boc-protected l-tyrosine, which was followed by esterification and alkylation of the phenol hydroxide. A number of novel chiral l-tyrosine porphyrins were obtained from the reactions of 2-tert-butoxycarbonylamino-3-(3-formyl-4-alkoxy-phenyl)-propionic acid ester with different dipyrrolylmethanes and the reaction of 5-(4-trifluoromethylphenyl)pyrromethane afforded the highest yield. The tyrosine porphyrins could be readily deprotected to afford the corresponding diacid or diamine derivatives. |
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Keywords: | porphyrin smallcaps" >l-tyrosine synthesis Reimer-Tiemann reaction |
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