保护团

2,2,2-三氯乙氧基羰基保护基 Troc Protecting Group

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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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

  1. 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

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

 

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LuWenjie

LuWenjie

京都大学药学博士,现某化学企业研究员,化学空间员工副代表,网页小编&翻译。

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