Allitol Allose

Allitol was characterized by its melting point, 149-150°, elementary analysis, and by the formation of a dibenzylidene derivative, which, after recrystallization from alcohol, melted at 249-250° on the Maquenne block. Later, Steiger and Reichstein7 repeated this synthesis of allitol and demonstrated the identity of the product with that obtained by the reduction of D-allose. 

The amount of each neutral monosaccharide in the samples can be calculated relative to the internal standard, allose, using response factors. The relative response of the detector for the individual alditol acetates can be calculated from the areas under the peaks for each alditol acetate, relative to the area under the peak for allitol acetate. There should be no peaks in the chromatogram of the water control and only one peak, corresponding to allitol hexaacetate from the internal standard allose, in the chromatogram of the TFA control. 

Pure allitol (meso configuration m. p. 150-151°) was described for the first time by Lespieau and Wiemann, who synthesized it by the hydroxylation of one of the stereoisomeric forms of divinylglycol. Its structure was established rigorously by Steiger and Reichstein when they demonstrated its identity with the product obtained by the reduction of D-allose. 

Benzamido-2-deoxy-D-allitol, A-155 2-Benzamido-2-deoxy-D-allose, A-156... 

An unequivocal synthesis of allitol was the reduction of D-allose with hydrogen and nickel catalyst 6S). The resulting hexitol agreed in its constants with the product made by Lespieau and Wiemann. 

---