Deduce the structure of the disaccharide melibiose from the following data: 1. Melibiose is a reducing sugar

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Deduce the structure of the disaccharide melibiose from the following data:
1. Melibiose is a reducing sugar that undergoes mutarotation and forms a phenylosazone.
2. Hydrolysis of melibiose with acid or with an a-galactosidase gives d-galactose and D-glucose.
3. Bromine water oxidation of melibiose gives melibionic acid. Hydrolysis of melibionic acid gives d-galactose and d-gluconic acid. Methylation of melibionic acid followed by hydrolysis gives 2, 3, 4, 6-tetra-O-methyl-d-galactose and 2, 3, 4, 5-tetra-O-methyl-D-gluconic acid.
4. Methylation and hydrolysis of melibiose give 2, 3, 4, 6-tetra-O-methyl- D-galactose and 2, 3, 4-tri-O-methyl-D-glucose.
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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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