文章基本信息

标题：New Method to Prepare N-t-Butoxycarbonyl Derivatives and the Corresponding Sulfur Analogs from di-t-Butyl Dicarbonate or di-t-Butyl Dithiol Dicarbonates and Amino Acids
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作者：D. Stanley Tarbell ; Yutaka Yamamoto ; Barry M. Pope 等
期刊名称：Proceedings of the National Academy of Sciences
印刷版ISSN：0027-8424
电子版ISSN：1091-6490
出版年度：1972
卷号：69
期号：3
页码：730-732
DOI：10.1073/pnas.69.3.730
语种：English
出版社：The National Academy of Sciences of the United States of America
摘要：Di-t-butyl dicarbonate and one of its dithiol analogs, practical methods of preparation for which are given, react with amino-acid esters to form the N-t-butoxycarbonyl (t-BOC) derivatives and the thiol analogs in good yield under mild conditions. The thiol analogs are stable to acidic conditions, which rapidly remove the t-BOC group itself. t-Butyl trimethylsilyl carbonate forms a (CH3)3Si ether from a N-thiol-t-BOC serine methyl ester. The N-thiol-t-BOC group can be removed from the --NHCOSR (R = t-butyl) by heating with peroxide-acetic acid. Action of the dicarbonates described above has not been attended by racemization in the cases examined. The two dicarbonates may be useful as agents for selective blocking and deblocking of amino or other groups.
关键词：blocking groups ; peptide synthesis