Direct, microwave-assisted substitution of anomeric nitrate-esters.

D Jamin Keith, Steven D Townsend

Carbohydrate research 2017 Apr 10

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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. Copyright © 2017 Elsevier Ltd. All rights reserved.