Analysis of sugar derivatives by chemical-ionization mass-spectrometry

D-Glucose diethyl dithioacetal (1), its penta-O-acetyl derivative (2), penta-O-acetyl-aldehydo-D-glucose (3), L-xylo-hexulose phenylosotriazole (4), 1,2:5,6-di-O-isopropylidene-D-mannitol (5), 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose (6), 1,2-O-isopropylidene-α-D-glucofuranose (7) and its triacetate (8), 1,6-anhydro-β-D-galactopyranose (9) and its triacetate (10), D-glucopyranose (11), methyl β-D-glucopyranoside tetraacetate (12), 1-thio-β-D-glucopyranose pentaacetate (13), β-D-fructofuranose pentaacetate (14), and raffinose hendecaacetate (15) have been examined by chemical-ionization mass-spectrometry with both isobutane and ammonia as ionizing intermediates. Extreme simplicity characterizes these spectra, and, in most instances, molecular-weight data are available from intact, protonor NH₄⁺capture ions; the limited fragmentation that occurs corresponds in large measure to simple dehydration or substituent-cleavage processes, and is strongly dependent upon the groups present, so that considerable information about the substituent groups in the sugar molecule may be inferred.