Wavelength-selective cleavage of o-nitrobenzyl and polyheteroaromatic benzyl protecting groups

被引：12
作者：
Piloto, Ana M. [1 ]
Costa, Susana P. G. [1 ]
Goncalves, M. Sameiro T. [1 ]
机构：
[1] Univ Minho, Ctr Chem, P-4710057 Braga, Portugal
来源：
TETRAHEDRON | 2014年 / 70卷 / 03期
关键词：
Photolabile protecting groups; Selective cleavage; o-Nitrobenzyl group; Acridine; Coumarin; REACTION-MECHANISMS; COUMARINS; RELEASE;
D O I：
10.1016/j.tet.2013.11.100
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Evaluation of the wavelength-selective cleavage of five photolabile protecting groups from two different families has been performed. Alanine, as a model bifunctional target molecule was masked at the amino terminal with o-nitrobenzyl group and at the carboxylic terminal with benzyl-type nitrogen and oxygen polyheteroaromatics, namely acridine, (thioxo)benzocoumarin and a coumarin built on the julolidine nucleus. The photosensitivity of the corresponding alanine conjugates was studied at selected wavelengths with HPLC/UV and H-1 NMR monitoring. The release of the fully deprotected molecule could be achieved by sequential irradiation in variable irradiation times, which were dependent on the heteroaromatic group used. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：650 / 657
页数：8
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