概要
2,2,2-三氯乙氧基羰基保护基(2,2,2-trichloroethoxycarbonyl, Troc)、它经常用于通过形成氨基甲酸酯来保护胺基。在某些情况下,它还用于酒精和苯酚上羟基的保护基。
对于强碱条件下的酯水解条件・强酸性条件・亲核条件・弱的氢化物的还原条件耐受性好,脱保护通常在锌-醋酸的单电子还原条件下进行。
基本文献
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- Windholz, T. B.; Johnston, D. B. R. Tetrahedron Lett. 1967, 8, 2555. doi:10.1016/S0040-4039(00)70346-7
- Carson, J. F. Synthesis 1981, 268. doi:10.1055/s-1981-29408
- Just, G.; Grozinger, K. Synthesis 1976, 457. DOI: 10.1055/s-1976-24080
反应机理
保护
2,2,2-三氯乙基氯甲酸酯(Troc-Cl)常用作反应试剂。加入吡啶或三乙胺作为碱并与胺反应。对于氨基酸的保护等,使用无机碱的Schotten-Baumann条件也很常见。
脱保护
在还原条件下使用锌粉 – 乙酸进行脱保护是常见的。 副产物为挥发性1,1-二氯乙烯和二氧化碳。
反応例
在许多保护基团存在下,可以选择性地除去Troc[1]。
参考文献
- Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1988, 53, 3108–3111. DOI: 10.1021/jo00248a037
关联书籍(日亚价格)
Greene’s Protective Groups in Organic Synthesis
- 著者Peter G. M. Wuts
- 参考価格¥ 12,342日元
- 出版社John Wiley & Sons Inc