jo6b02038_si_004.cif (19.71 kB)
Synthesis of d‑Galactosamine and d‑Allosamine Derivatives via a Microwave-Assisted Preparation of 1,6-Anhydroglucosamine
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posted on 2016-10-24, 00:00 authored by Vijay
M. Dhurandhare, Yuh-Sheng Wen, Sachin
D. Gawande, Pin-Hsuan Liao, Cheng-Chung WangWe 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
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