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Journal Article
Research Support, Non-U.S. Gov't
Synthesis of d-Galactosamine and d-Allosamine Derivatives via a Microwave-Assisted Preparation of 1,6-Anhydroglucosamine.
Journal of Organic Chemistry 2016 November 19
We report a microwave-assisted intramolecular anomeric protection (iMAP) of glucosamine, which facilitates concise transformation of 1,6-anhydroglucosamine into 1,6-anhydrogalactosamine and 1,6-anhydroallosamine. The iMAP simultaneously obviates both the O1 and O6 protection, and the differentiation between O3 and O4 can be well-controlled by the N2 functionality because of the hydrogen bonding between N2 and O4. Epimerization of O4 afforded the galactosamine derivative and that of O3 yielded allosamine.
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