Alcohols immobilization onto 2-chlorotritylchloride resin under microwave irradiation

作者：Rizzi Luca^*; Cendic Katarina; Vaiana Nadia; Romeo Sergio

来源：Tetrahedron Letters, 2011, 52(22): 2808-2811.

DOI：10.1016/j.tetlet.2011.03.113

• Solid phase synthesis
• 2-Chlorotritylchloride resin
• Alcohol
• Microwave
• Cyclic peptide

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.

• 出版日期2011-6-1