Abstract
Gas–liquid partition chromatography has been used to separate all of the possible tetra- and tri-O-methyl ethers of methyl α- and β-D-glucopyranoside. Anomeric methyl glycosides of each isomer were well separated except those of 3,4,6-tri-O-methyl-D-glucose. The six di-O-methyl-D-glucopyranoses were partially resolved as their methyl glycosides. The four possible mono-O-methyl-D-glucopyranoses were completely resolved after conversion to the corresponding mono-O-methyl-penta-O-acetyl-D-glucitols, a series of compounds which, except for the 6-O-methyl isomer, have not been reported previously. Quantitative estimations of mixtures containing varying amounts of methyl-2,3,4-tri-O-methyl-β-D-xylopyranoside and methyl-2,3,4,6-tetra-O-methyl-α-D-glucopyranoside showed that molar ratios of components in a mixture could be determined with a mean deviation of ±0.5 in 100.
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