title: Direct, microwave-assisted substitution of anomeric nitrate-esters.
abstract: 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.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA.
authors.forename: D Jamin
authors.initials: DJ
authors.lastname: Keith
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA; Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37232, USA. Electronic address: steven.d.townsend@vanderbilt.edu.
authors.forename: Steven D
authors.initials: SD
authors.lastname: Townsend
mesh_terms: D001386:Azides / Q000737:chemistry*; D002236:Carbohydrate Conformation; D004952:Esters; D006868:Hydrolysis; D008872:Microwaves
chemical_list: D001386:Azides; D004952:Esters
keywords: Azido-nitration; Glycosidation; Glycosylation; Hydrolysis; Nitrate-ester; Trichloroacetimidate