By Claude S. Hudson, etc.
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 5
Methyl 2,3-anhydro-4,6-benzylidene-a-~-mannovide (LXIV), upon treatment with sodium thiomethoxide, was converted into methyl 3-methylthio-4,6-benzylidene-a-~-altroside(LXV) which, after desulfurization and rebenzylidenation, gave methyl 3-desoxy-4,6-benzylidene-a-~-mannoside (LXVI). Methylation of LXV with methyl iodide and silver oxide followed by desulfurization gave methyl 2-methyl-3-desoxy-4,6benzylidene-a-D-mannoside in poor yield. Maehly and Reichsteinel have found that treatment of methyl 2-methylthio-4,6-benzylidene-a-~-idoside (LXVII) with Raney nickel (60) H.
It is of interest that similar enzymes, capable of exchanging glycosidic linkages, appear to be involved in the synthesis of some polysaccharides. 4~The reactions may be written as follows : “ (C6HloOdn n CiIHIaOiI (D-glucose-1-D-fructoside) (dextran) (CaHtoO& n CiaHziOii (D-glucose-1-D-fructoside) (levan) --f + n(D-fructose) CsHlzOe + n(D-glucose) CsHllOs Although these reactions normally go almost completely from:left to right, indirect evidence has been presented for their reversible nature.
Courtois, Bull. SOC. , 10, 245 (1943); Compt. , 214, 366 (1942). 32 W. 2. HASSID AND M. DOUDOROFF Hudsonlo showed that the mutarotation of fructose in water at 30" is eleven times faster than that of glucose. He therefore assumed that in a sucrose solution which is undergoing very rapid inversion with invertase at that temperature, practically all of the fructose has reached equilibrium and exists as a mixture of its a and p forms, while the glucose is being liberated in only one form which, however, slowly passes to its a, p equilibrium mixture.
Advances in Carbohydrate Chemistry, Vol. 5 by Claude S. Hudson, etc.