(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) Esters - a Novel Carboxyl Protecting Group

Michael Wagner; Horst Kunz

doi:10.1055/s-2000-6513

Synlett 2000; 2000(3): 400-402
DOI: 10.1055/s-2000-6513

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(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) Esters - a Novel Carboxyl Protecting Group

Michael Wagner^* , Horst Kunz

^*Institut für Organische Chemie der Universität Mainz, Duisbergweg 10-14, D-55099 Mainz, Germany; Fax +49 61 31 39 48 76; E-mail: hokunz@mail.uni-mainz.de

Abstract

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A novel silicon-containing protecting group based on the known 2-(trimethylsilyl)ethyl system has been developed for the protection of the carboxylic group, e.g. in peptide chemistry. The new protecting group can be cleaved by treatment with tetra-n-butylammonium fluoride much more rapidly than the known 2-(trimethylsilyl)ethyl group, leading to less side reactions.

carboxyl protecting groups - 2-(silyl)ethyl esters - peptide synthesis - fluoride-induced elimination

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