Trehalose is a nonreducing disaccharide (C12H22O11) isolated from the poisonous mushroom Amanita muscaria. Treatment with an a@glucosidase converts trehalose to two molecules of glucose, but no reaction occurs when trehalose is treated with a b@glucosidase.When trehalose is methylated by dimethyl sulfate in mild base and then hydrolyzed,the only product is 2,3,4,6-tetra-O-methylglucose. Propose a complete structure andsystematic name for trehalose.

Trehalose is a nonreducing disaccharide (C12H22O11) isolated from the poisonous mushroom Amanita muscaria. Treatment with an a@glucosidase converts trehalose to two molecules of glucose, but no reaction occurs when trehalose is treated with a b@glucosidase.When trehalose is methylated by dimethyl sulfate in mild base and then hydrolyzed,the only product is 2,3,4,6-tetra-O-methylglucose. Propose a complete structure andsystematic name for trehalose.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter25: Carbohydrates

Section: Chapter Questions

Problem 25.36P

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