Efficient trapping of the liberated fluoride ions is the key to the synthesis of the hexakis(onio)‐substituted benzene derivative 1 in 92% yield from hexafluorobenzene and dimethylaminopyridine. In the solid state one of the triflate counterions of 1 is located above and one below the central benzene ring to give a triple‐decker‐type structure.
ether phase decanted. The precipitate was washed several times with ether and finally dried to give the deprotected product as a white powder (13 mg. 91 %). The reductive amination was carried out using a modification of a published procedure [13]. In a typical experiment, the protected peptide la (10 pmol) was dissolved in 2 mL of a 10: 1 mixture of 0.1 M phosphate buffer (pH 6.0) and CH3CN. To this peptide solution were added the carbohydrate (200 pmol) dissolved in 2 mL of the Same buffer and sodium cyanoborohydride (200 pmol) as a solid. The mixture was stirred at room temperature and progress of the coupling reaction monltored by analytical HPLC. The glycopeptides were purified by semipreparative HPLC and characterized by ESI-MS. syntheses solid-phase[l] I.
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