%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