title: Synthesis of d-Galactosamine and d-Allosamine Derivatives via a Microwave-Assisted Preparation of 1,6-Anhydroglucosamine.
abstract: 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.
authors: Institute of Chemistry, Academia Sinica , Taipei 115, Taiwan.|Chemical Biology and Molecular Biophysics, Taiwan International Graduate Program (TIGP), Academia Sinica , 128, Section 2, Academia Road, Taipei 115, Taiwan.|Institute of Bioinformatics and Structural Biology, National Tsing Hua University , 101, Section 2, Kuang-Fu Road, Hsinchu 300, Taiwan.
authors: Vijay M
authors: VM
authors: Dhurandhare
authors: Institute of Chemistry, Academia Sinica , Taipei 115, Taiwan.
authors: Yuh-Sheng
authors: YS
authors: Wen
authors: Institute of Chemistry, Academia Sinica , Taipei 115, Taiwan.
authors: Sachin D
authors: SD
authors: Gawande
authors: Institute of Chemistry, Academia Sinica , Taipei 115, Taiwan.
authors: Pin-Hsuan
authors: PH
authors: Liao
authors: Institute of Chemistry, Academia Sinica , Taipei 115, Taiwan.|Chemical Biology and Molecular Biophysics, Taiwan International Graduate Program (TIGP), Academia Sinica , 128, Section 2, Academia Road, Taipei 115, Taiwan.
authors: Cheng-Chung
authors: CC
authors: Wang