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The following experimental results were obtained from tests on a rare disacchari

ID: 844698 • Letter: T

Question


The following experimental results were obtained from tests on a rare disaccharide, olaose, isolated from a lichen growing on stones in the parking lot of Open Learning in Kamloops, BC. Acid catalysis of olaose gave one mole of D-glucose and one mole of D-idose. Olaose is a reducing sugar, as it gave a positive reaction with Tollen s reagent. Olaose is hydrolyzed by beta-glucosidases. Methylation of olaose followed by acid hydrolysis gave 2, 3, 4, 6-tetra-O-methyl-D-glucose and 2,4,6-tri-O-methyl-D-idose. The Fischer projection formulas for D-glucose and D-idose are given below. Assume that these monosaccharides are in the pyranose (six-membered ring) form. Deduce the structure of olaose and draw' its Haworth projection formula. Explain your reasoning.

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