Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker
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Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker. / Crestey, François; Ottesen, Lars Korsgaard; Jaroszewski, Jerzy Witold; Franzyk, Henrik.
In: Tetrahedron Letters, Vol. 49, No. 41, 2008, p. 5890-5893.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker
AU - Crestey, François
AU - Ottesen, Lars Korsgaard
AU - Jaroszewski, Jerzy Witold
AU - Franzyk, Henrik
PY - 2008
Y1 - 2008
N2 - 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.
AB - 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.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1016/j.tetlet.2008.07.130
DO - 10.1016/j.tetlet.2008.07.130
M3 - Journal article
VL - 49
SP - 5890
EP - 5893
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 41
ER -
ID: 10159153