Synthesis and analytical characterization of the sodium salt of heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomalto-heptaose, a chiral resolving agent candidate for capillary electrophoresis

A pure, single isomer, strong electrolyte chiral resolving agent candidate for capillary electrophoresis, the sodium salt of heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomaltoheptaose has been synthesized on the 100-g scale, in greater than 97% purity, through heptakis(2,6-di-O-tert-butyldimethylsily)cyclomaltoheptaose, heptakis(2-O-methyl-3,6-diO-tert-butyldimethylsilyl)cyclomaltoheptaose and heptakis(2-O-methyl)cyclomaltoheptaose intermediates. The structural identity of each intermediate and the final product was conclusively established by high-resolution MALDI-TOF mass;spectrometry, variable-temperature H-1 and C-13 NMR spectroscopy and X-ray crystallography. The purity of each intermediate and the final product was determined by gradient high-performance liquid chromatography (HPLC) and indirect UV detection capillary electrophoresis. (C) 2000 Elsevier Science Ltd. All rights reserved.