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Solved: An unknown disaccharide gives a positive Tollens

Chapter 21, Problem 61P

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QUESTION:

Problem 61P

An unknown disaccharide gives a positive Tollens test. A glycosidase hydrolyzes it to D-galactose and D-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactoseand 2,3,4-tri-O-methylmannose. Propose a structure for the disaccharide.

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QUESTION:

Problem 61P

An unknown disaccharide gives a positive Tollens test. A glycosidase hydrolyzes it to D-galactose and D-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactoseand 2,3,4-tri-O-methylmannose. Propose a structure for the disaccharide.

ANSWER:

Solution 61P

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