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

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

  • François Crestey
  • Lars Korsgaard Ottesen
  • Jerzy Witold Jaroszewski
  • Franzyk, Henrik
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.
OriginalsprogEngelsk
TidsskriftTetrahedron Letters
Vol/bind49
Udgave nummer41
Sider (fra-til)5890-5893
ISSN0040-4039
DOI
StatusUdgivet - 2008

ID: 10159153