Synthesis of d‑Galactosamine and d‑Allosamine Derivatives
via a Microwave-Assisted Preparation
of 1,6-Anhydroglucosamine
Vijay
M. Dhurandhare
Yuh-Sheng Wen
Sachin
D. Gawande
Pin-Hsuan Liao
Cheng-Chung Wang
10.1021/acs.joc.6b02038.s002
https://acs.figshare.com/articles/dataset/Synthesis_of_d_Galactosamine_and_d_Allosamine_Derivatives_via_a_Microwave-Assisted_Preparation_of_1_6-Anhydroglucosamine/4206636
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 <i>O</i>1 and <i>O</i>6 protection, and the differentiation between <i>O</i>3 and <i>O</i>4 can be well-controlled by the <i>N</i>2 functionality because of the hydrogen bonding between <i>N</i>2 and <i>O</i>4. Epimerization of <i>O</i>4 afforded
the galactosamine derivative and that of <i>O</i>3 yielded
allosamine.
2016-10-24 00:00:00
O 4. Epimerization
obviate
Anhydroglucosamine
differentiation
Derivative
microwave-assisted intramolecular anomeric protection
well-controlled
anhydroglucosamine
Microwave-Assisted
transformation
Synthesi
Preparation
N 2 functionality
O 3
O 6 protection
O 4
anhydrogalactosamine
iMAP
glucosamine
galactosamine
anhydroallosamine
allosamine