Direct, microwave-assisted substitution of anomeric nitrate-esters

A series of carbohydrate 2-azido-1-nitrate-esters, protected at the C-3, C-4, and C-6 positions, were hydrolyzed thermally under reagent free conditions. This preliminary result was extended to direct exchange of the 1-nitrate-ester modality for alcohol, alkoxy, and azide coupling partners with mini...

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Bibliographic Details
Published in:Carbohydrate research 2017-04, Vol.442, p.20-24
Main Authors: Keith, D. Jamin, Townsend, Steven D.
Format: Article
Language:English
Subjects:
Azides - chemistry
Azido-nitration
Carbohydrate Conformation
Esters
Glycosidation
Glycosylation
Hydrolysis
Microwaves
Nitrate-ester
Trichloroacetimidate
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Summary:A series of carbohydrate 2-azido-1-nitrate-esters, protected at the C-3, C-4, and C-6 positions, were hydrolyzed thermally under reagent free conditions. This preliminary result was extended to direct exchange of the 1-nitrate-ester modality for alcohol, alkoxy, and azide coupling partners with minimal purification. While direct glycosylation of nitrate esters ultimately proved unsuccessful, we have demonstrated that an anomeric nitrate-ester can be converted directly to a trichloroacetimidate in a short and simple one-pot procedure, bypassing lower yielding two-step sequences. [Display omitted] •Short Reaction Times.•Minimal Reagents.•70–100% yield.•One-Pot Conversion of a Nitrate-Ester to a Schmidt Imidate.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2017.02.005