A general approach to L-tyrosine plorphyrins

被引：14

作者：

Chen, H ^{[1
]}

Shao, XB ^{[1
]}

Jiang, XK ^{[1
]}

Li, ZT ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2003年 / 59卷 / 19期

基金：

中国国家自然科学基金;

关键词：

L-tyrosine; synthesis; Reimer-Tiemann reaction;

D O I：

10.1016/S0040-4020(03)00487-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 bexyl 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. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3505 / 3510

页数：6

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