Alcohols immobilization onto 2-chlorotritylchloride resin under microwave irradiation |
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Authors: | Luca Rizzi Katarina CendicNadia Vaiana Sergio Romeo |
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Affiliation: | Dipartimento di Scienze Farmaceutiche “Pietro Pratesi”, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milan, Italy |
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Abstract: | 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. |
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Keywords: | Solid phase synthesis 2-Chlorotritylchloride resin Alcohol Microwave Cyclic peptide |
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