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

Abstract

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-butyldimethylsilyl)cyclomaltoheptaose, heptakis(2- O-methyl-3,6-di- O- 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 1H and 13C 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.