HYDROGENOLYSIS OF CARBOHYDRATES: III. FURTHER OBSERVATIONS ON THE REDUCTION OF METHYL α-D- GLUCOPYRANOSIDE

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Abstract
The hydrogenolysis of methyl α-D-glucopyranoside at 180° to 220 °C. was found to yield in addition to the polyols obtained at 240° substantial quantities of hydro-D-glucal (2-deoxy-1,5-anhydro-D-sorbitol), smaller amounts of 2-deoxymethyl glucoside, and the hitherto unknown hydro-D-altral, as well as trace amounts of several other unidentified deoxy-glycosides and 1,5-anhydrohexitols. These findings accordingly revise the reduction mechanism proposed earlier and show that inversion of one or more hydroxyl groups can occur during the hydrogenolysis.

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