%0 Generic %A Dhurandhare, Vijay M. %A Wen, Yuh-Sheng %A Gawande, Sachin D. %A Liao, Pin-Hsuan %A Wang, Cheng-Chung %D 2016 %T Synthesis of d‑Galactosamine and d‑Allosamine Derivatives via a Microwave-Assisted Preparation of 1,6-Anhydroglucosamine %U https://acs.figshare.com/articles/dataset/Synthesis_of_d_Galactosamine_and_d_Allosamine_Derivatives_via_a_Microwave-Assisted_Preparation_of_1_6-Anhydroglucosamine/4206639 %R 10.1021/acs.joc.6b02038.s004 %2 https://acs.figshare.com/ndownloader/files/6864189 %K O 4. Epimerization %K obviate %K Anhydroglucosamine %K differentiation %K Derivative %K microwave-assisted intramolecular anomeric protection %K well-controlled %K anhydroglucosamine %K Microwave-Assisted %K transformation %K Synthesi %K Preparation %K N 2 functionality %K O 3 %K O 6 protection %K O 4 %K anhydrogalactosamine %K iMAP %K glucosamine %K galactosamine %K anhydroallosamine %K allosamine %X 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. %I ACS Publications