Question: Gentiobiose has the molecular formula C12H22O11 and has been isolated from gentian root and by hydrolysis of amygdalin. Gentiobiose exists in two different forms, one

Gentiobiose has the molecular formula C12H22O11 and has been isolated from gentian root and by hydrolysis of amygdalin. Gentiobiose exists in two different forms, one melting at 86°C and the other at 190°C. The lower melting form is dextrorotatory ([a] 22/D + 16°), the higher melting one is levorotatory ([a] 22/D -6°). The rotation of an aqueous solution of either form, however, gradually changes until a final value of ([a] 22/D + 9.6° is observed. Hydrolysis of gentiobiose is efficiently catalyzed by emulsin and produces two moles of D-glucose per mole of gentiobiose. Gentiobiose forms an octamethyl ether, which on hydrolysis in dilute acid yields 2, 3, 4, 6-tetra-Omethyl-D-glucose and 2, 3, 4-tri-O-methyl-D-glucose. What is the structure of gentiobiose?

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