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Chim. Acta, 30, 496 (1947). DESULFURIZATION BY RANEY NICKEL 21 prepared from a four-fold quantity of Raney alloy (approximately 50% nickel) caused only desulfurization and gave methyl 2-desoxy-4,6benzylidene-a-D-guloside (LXVIII) in 57 % yield. When the Raney nickel prepared from a thirty-fold quantity of alloy was used the benzylidene group also was removed and the product was methyl 2-desoxya-D-guloside (LXIX). Other idose derivatives were hydrogenated by H & F I HA- HCO-- c: H 0 LXIV LXV H OCHa H CHIS H I G AHZ I I I LOkHz LXVIII C H s O F HobH b H SCHs + - 0 b H Gut, Prins and Reichstein:62 methyl 3-methylthio-4,6-benzylidene-@-~idoside (LXX) with a four-fold quantity of Raney nickel (prepared from an eight-fold quantity of alloy) gave methyl 3-desoxy-4,6-benzylidene-fl-D-idoside (LXXI) in 92% yield; use of a large excess of nickel resulted in simultaneous debenzylidenation.
Recent data obtained through periodate oxidatione has proved this assumption to be correct. It was found that when sucrose is oxidized with sodium metaperiodate, three moles of periodate were consumed and one mole of formic acid was produced in the reaction. These results are consistent with a disaccharide consisting of a glucopyranose and a fructofuranose unit. Any other ring configuration for either the aldose or the ketose component would give different results. Since both hexose units in sucrose are joined through the carbonyl groups, the disaccharide is at one and the same time a glucoside and a fructoside.
XaOH L LH2OAc LI of the free crystalline 1,5-anhydro-~-galactitol (L) were found to differ markedly from those which Freudenberg and Rogerss3had reported for the comparable substance which they had obtained by reduction of tetraacetyl-2-hydroxy-~-galactal (XLVIII) and led to the conclusion that the product of these authors was 1,5-anhydro-~-talitol (XLIX). An unequivocal synthesis of 1,5-anhydro-~-talitol~~ has since confirmed this conclusion. (52) (53) (54) 70,2201 R. C. Hockett and Maryalice Conley, J .