By Claude S. Hudson, etc.
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 5
Maehly and Reichsteinel have found that treatment of methyl 2-methylthio-4,6-benzylidene-a-~-idoside (LXVII) with Raney nickel (60) H. R. Bolliger and D. A. Prins, Helv. Chim. dg, 1061 (1946). (81) A. C. Maehly and T. Reichstein, Helv. 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).
S. Hudson, J . Am. Chem. ,69, 994 (1937); 62, 958 (1940); R. M. Hann, W. D. Maclay and C. S. , 61, 2432 (1939). (39) H. W. Raybin, J . Am. Chem. , 66, 2603 (1933); 69, 1402 (1937). SYNTHESIS O F SUCROSE 41 an additional -CH20H group attached t o carbon atom 5 of the ring of the ketose moiety. 3. D-Glucosyh-araboketoside Another non-reducing disaccharide has been recently synthesized as a result of enzymatic action of a P. z8 Like the other two disaccharides, it does not reduce Fehling or alkaline ferricyanide solution and it is not affected by invertase.
Pigman, J . Research Natl. Bur. Standards, 20, 773 (1938). (35) A. Gottschalk, Auetralian J . Exptl. Biol. Med. , 20, 139 (1943). (36) W. Z. , 13, 641 (1938). 8. Most of the unreacted D-xylose waa separated by crystallization, leaving a sirup consisting chiefly of D-xyloketose. 40 W. 2. HASSID AND M. 88 A disaccharide consisting of glucopyranose and xyloketofuranose glycosidically united through positions 1 and 2 of the aldose and ketose monosaccharides, respectively, would possess three adjacent free hydroxyls on carbon atoms 2, 3, and 4 in the glucose residue and two free hydroxyls on carbon atoms 3 and 4 in the xyloketose residue.
Advances in Carbohydrate Chemistry, Vol. 5 by Claude S. Hudson, etc.