Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker

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François Crestey, Lars Korsgaard Ottesen, Jerzy Witold Jaroszewski, Henrik Franzyk

The Letter describes an improved, rapid and mild strategy for the loading of primary alcohols onto a polystyrene trityl resin via a highly reactive trityl bromide linker. This protocol facilitates an efficient resin loading even of acid-sensitive or heat-labile alcohols, which otherwise require expensive or non-commercial resin types. Secondary alcohols were only attached in moderate to low yields, while attempts to load a tertiary alcohol expectedly failed. Importantly, selective attachment of diols via a primary alcohol group in the presence of more hindered alcohol groups proved possible. The effects of activation time and reagent excess as well as alcohol structure were investigated. This improved method provides a convenient access to O-linked resin-bound N-Fmoc-protected amino alcohols that may be employed in SPS of peptides with C-terminal alcohol functionalities. In the case of a sensitive alcohol containing an activated aziridine functionality, the use of the trityl bromide linker proved superior to a recently described silver triflate-assisted trityl chloride resin-based procedure.
Original languageEnglish
JournalTetrahedron Letters
Volume49
Issue number41
Pages (from-to)5890-5893
ISSN0040-4039
DOIs
Publication statusPublished - 2008

ID: 10159153