Prenyl carbamates:: preparation and deprotection
Prenyl carbamates:: preparation and deprotection
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DOI：
10.1016/j.tet.2004.03.028
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发表时间：
2004-05-03
期刊：
影响因子：
2.1
通讯作者：
Vatèle, JM
中科院分区：
文献类型：
--
作者：
Vatèle, JM
异戊烯基氧羰基咪唑（PreocIm）和异戊烯基对硝基苯基碳酸酯（PreocOC（6）H（4）p-NO2）是不稳定的异戊烯基氯甲酸酯的两种替代物，可以有效地将异戊烯基氧羰基引入各种伯胺和仲胺中。氨基甲酸异戊烯酯的脱保护容易通过以下方式实现：首先用碘在甲醇中将其转化为氨基甲酸2-碘-3-甲氧基-3-甲基丁酯，然后用锌粉还原性β-消除。这些反应条件与许多官能团如Boc和Cbz氨基甲酸酯、硫化物、双键、吲哚和芳族醚的存在相容。(C)2004 Elsevier Ltd.保留所有权利。
Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.