AMINO-ACIDS AND PEPTIDES .41. EXAMINATION OF SOME NEW AMINO-PROTECTING GROUPS

被引:6
作者
COYLE, S [1 ]
KELLER, O [1 ]
YOUNG, GT [1 ]
机构
[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 06期
关键词
D O I
10.1039/p19790001459
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In an investigation of the effect of the introduction of basic sites on the stability of alkoxycarbonyl groups to acid the following new amino-protecting groups have been examined: di-2-pyridylmethoxycarbonyl [e.g. (1)], 4-pyridylisopropoxycarbonyl [e.g. (4)], 3-diethylamino-1,1- diphenylpropoxycarbonyl [e.g. (10)], and 1,4-dimethylpiperidin-4-yloxycarbonyl [e.g. (13)]. In each case the stability to acid is considerably enhanced. The last-named group provides protection which is more stable to trifluoroacetic acid than is the t-butoxycarbonyl group, is stable to hydrogenolysis, and is cleaved by hydrogen bromide in acetic acid. In an investigation of amino-protecting groups designed to increase the solubility of derivatives by the incorporation of dimethylcarbamoyl substituents, the preparation of 2-dimethylcarbamoylethyl-isopropoxycarbonyl [e.g. (18)] and 2- dimethylcarbamoylbenzyloxycarbonyl [e.g. (24)] amino-acids is reported.
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页码:1459 / 1463
页数:5
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