By Claude S. Hudso (ed.), Sidney M. Canto (ed.)
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Extra info for Advances in Carbohydrate Chemistry, Vol. 6
3. 2,6-Dimethyl-~-Galactose The easily prepared 3,4-isopropylidene derivatives of the a and p methyl-D-galactopyranosides form the starting points of the s y n t h e ~ i s . ~ . ~ Methylation of either substance, followed by hydrolytic removal of first the isopropylidene and then the glycosidic methyl radicals leads t o crystalline 2,6-dimethyl-~-galactose. Since the above mentioned syn(25) D. J. Bell, J . Chem. , 692 (1945). (26) See numerous papers by F. Smith, by J. K. N. Jones, and by E. L.
Chem. , 692 (1945). (26) See numerous papers by F. Smith, by J. K. N. Jones, and by E. L. Hirst, and their collaborators, in the Journal of the Chemical Society. (27) E. Baldwin and D. J. Bell, J. Chem. ,1461 (1938). (28) D. J. Bell and E. Baldwin, J. Chem. ,125 (1941). 18 D. J. BELL theses were recorded, this sugar has been isolated from the hydrolysis products of a methylated polysaccharide from Gigartina stellata by Dewar and PercivaLZ9 Discrepancies between the melting points found for various specimens led Bellaoto reexamine the synthesis of this sugar.
Then Koenigs and Knorrs6prepared the more useful tetraacetyl-a-D-glucopyranosyl bromide by the action of acetyl bromide on D-glucose. They found that if a solution of the bromide in methanol was allowed to stand for some time, methyl p-n-glucopyranoside was formed, the first case of the synthesis of an alkyl glycoside using the acylglycosyl halides. Koenigs and Knorr also found that dry, powdered silver carbonate, or hot, dry pyridine or a concentrated aqueous solution of silver nitrate were all three useful as condensing agents when tetraacetyl-a-D-glucopyranosyl bromide was dissolved in absolute methanol.