The immobilization of alcohols onto 2-chlorotritylchloride resin using microwave irradiation was studied. Three different Fmoc-aminoalcohols were tested: the phenol-like Fmoc-tyramine, the primary alcohol Fmoc-ethanolamine, and the secondary alcohol Fmoc-4-hydroxypiperidine. Several reaction conditions were evaluated: different bases, reaction times, temperatures, and concentrations. Microwave immobilization resulted is effective in binding to the resin all three types of alcohols with loadings which were superior or comparable to the 'classical' methods in shorter time and without employing toxic and racemizing reagents. This method resulted also useful for the immobilization, through the hydroxyl group, of FmocTyrOAll, FmocSerOAll, and FmocThrOAll, important building blocks for the synthesis of cyclic peptides.
Alcohols immobilization onto 2-chlorotritylchloridenext term resin under microwave irradiation / L. Rizzi, K. Cendic, N. Vaiana, S. Romeo. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 52:22(2011 Jun 01), pp. 2808-2811.
|Titolo:||Alcohols immobilization onto 2-chlorotritylchloridenext term resin under microwave irradiation|
RIZZI, LUCA (Primo)
CENDIC, KATARINA (Secondo)
VAIANA, NADIA (Penultimo)
ROMEO, SERGIO (Ultimo)
|Parole Chiave:||2-Chlorotritylchloride resin; Alcohol; Cyclic peptide; Microwave; Solid phase synthesis|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||1-giu-2011|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.tetlet.2011.03.113|
|Appare nelle tipologie:||01 - Articolo su periodico|