Synthesis of d‑Galactosamine and d‑Allosamine Derivatives via a Microwave-Assisted Preparation of 1,6-Anhydroglucosamine
journal contributionposted on 24.10.2016, 00:00 by Vijay M. Dhurandhare, Yuh-Sheng Wen, Sachin D. Gawande, Pin-Hsuan Liao, Cheng-Chung Wang
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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O 4. EpimerizationobviateAnhydroglucosaminedifferentiationDerivativemicrowave-assisted intramolecular anomeric protectionwell-controlledanhydroglucosamineMicrowave-AssistedtransformationSynthesiPreparationN 2 functionalityO 3O 6 protectionO 4anhydrogalactosamineiMAPglucosaminegalactosamineanhydroallosamineallosamine