Synthesis and characterisation of a partially methylated dodecyl thiomaltotrioside derivative as a precursor of cyclodextrin analogue

Abstract

Due to the enermous roles of cyclodextrin combining with small organic molecules, more recent interests study about the manipulation of cyclodextrin structure giving better performance for any kinds of field but they presented long synthetis steps as producing the precursors. This study points out the synthesis of precursor of β-cyclodextrin analouges with maltotriose as raw materials giving the short synthesis steps. The product structures were analysed by Fourier Transform Infrared (FTIR) Specstroscopy,and characterised by 1H-, 13C- NMR, COSY NMR, and ESI Mass Spectroscopy. The result showed that O-acetylation reaction produced maltotriose derivative 1 (95%), thioglycosidation reaction produced maltotriose derivative 2 (54%), de-acetylation reaction produced maltotriose derivative 3 (97%), O-benzylidation reaction produced a mixture of maltotriose derivatives 4, O- methylation reaction produced maltotriose derivative 5 (46%) and de-benzylidation reaction produced maltotriose derivative 6 (85%).